COMPOUNDS OF FORMULA I, MIXTURE, AGROCHEMICAL COMPOSITION AND METHOD TO COMBAT HARMFUL PHYTOPATHOGEN

专利摘要:
use of formula I compounds, formula I compounds, mixture, agrochemical composition and method to combat harmful phytopathogenic fungi. substituted oxadiazoles to combat phytopathogenic fungi. The present invention relates to the use of the compounds of the formula I or the n-oxides, or the agriculturally acceptable salts thereof, for combating harmful phytopathogenic fungi, wherein the variables are defined as given in the specification and claims. Another present invention relates to certain oxadiazole compounds, to mixtures comprising at least one compound of formula I and at least one additional pesticide active substance selected from the group consisting of herbicides, phytotoxicity protectants, fungicides, insecticides and regulators of plant growth; and to agrochemical compositions which comprise at least one compound of formula I and to agrochemical compositions which further comprise seeds.
公开号:BR112018008449B1
申请号:R112018008449-2
申请日:2016-11-16
公开日:2021-07-06
发明作者:Manuel KRETSCHMER；Christine WIEBE；Wassilios Grammenos；Ana Escribano Cuesta；Maria Angelica Quintero Palomar；Ian Robert Craig；Marcus Fehr；Tobias MENTZEL；Bernd Mueller；Christian Harald Winter；Violeta TERTERYAN-SEISER；Jan Klaas Lohmann；Erica CAMBEIS；Thomas Grote
申请人:Basf Se；
IPC主号:

专利说明:

[0001] The present invention relates to the use of oxadiazoles of the formula I or an N-oxide and/or their use in agriculture to control phytopathogenic fungi or a method to combat harmful phytopathogenic fungi, a process which comprises treating the fungi or the materials, plants, soil or seeds to be protected from fungal attack, with an effective amount of at least one compound of formula I or an N-oxide, or an agriculturally acceptable salt thereof; the present invention also relates to mixtures comprising at least one such compound of formula I and at least one additional pesticide active substance selected from the group consisting of herbicides, phytotoxicity protectants, fungicides, insecticides and plant growth regulators; and to agrochemical compositions comprising at least one such compound of formula I and to agrochemical compositions further comprising seeds.
[0002] EP 2 764 32 A2 refers to 3-phenyl-5-trifluoromethylaxadiazole derivatives and their uses in combating phytopathogenic microorganisms. WO 2013/008162 describes trifluoromethyl-oxadiazole derivatives with HDAC4 inhibitory activity and their medical use, particularly in the treatment of Huntington's disease, muscle atrophy and diabetes/metabolic syndrome. WO 11/088192, WO 2011/088181 describe the medicinal use of trifluoromethyl-oxadiazole derivatives. A use to control phytopathogenic fungi is not described. WO 2015/185485 was published after the filing date of the present application and describes the use of certain substituted oxadiazoles to combat phytopathogenic fungi.
[0003] In many cases, particularly at low application rates, the fungicidal activity of known fungicidal compounds is unsatisfactory. Based on this, it was an aim of the present invention to provide compounds with improved activity and/or a broader spectrum of activity against phytopathogenic fungi. This objective is achieved by formula I oxadiazoles and/or their agriculturally useful salts for the control of phytopathogenic fungi.
[0004] Therefore, the present invention relates to the use of the compounds of the formula I
wherein: A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1, 2, 3 or 4 identical or different groups RA; where RA is halogen, cyano, NO2, OH, NH2, SH, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C6 alkenyl, C2-C6 alkynyl, cycloalkyl C3-C8 or C3-C8 cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1, 2, 3 or 4 identical or different Ra groups; wherein Ra is halogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1C6 haloalkylthio or C3-C8 cycloalkyl; R2 independently of one another are hydrogen, C1C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C(=O)-(C1-C6 alkyl), C(=O)- (C1-C6 alkoxy), phenyl-C1-C4 alkyl, heteroaryl-C1-C4 alkyl, phenyl, naphthyl, or a saturated, partially unsaturated or mono- or bicyclic aromatic 3- to 10-membered heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include, in addition to carbon atoms, further 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 ring member atoms of heterocycle carbon may be substituted by 1 or 2 groups independently selected from C(=O) and C(=S); and wherein the heteroaryl group in the heteroaryl-C1-C4 alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include in addition to carbon atoms 1, 2, 3 or 4 heteroatoms selected a from N, O and S as ring member atoms; and wherein any of the aforementioned aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different R1a groups; or R1 and R2 together with the nitrogen atom to which they are attached form a 3- to 7-membered saturated or partially unsaturated mono- or bicyclic heterocycle, wherein the heterocycle includes, in addition to a nitrogen atom and one or more carbon atoms, no other heteroatoms or 1, 2 or 3 other heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=O) and C(=S); and wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different R1a groups; wherein R1a is halogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1C6 haloalkylthio, C3-C8 cycloalkyl, NHSO2- C1-C4 alkyl, (C=O)-(C1-C4 alkyl) C(=O)-(C1-C4 alkoxy) or C1-C6 alkylsulfonyl;R3 is H, C1-C4 alkyl, C1-C4 haloalkyl;R4 is H, C1-C4 alkyl, C1-C4 haloalkyl; or the N-oxides, or agriculturally acceptable salts thereof, to combat harmful phytopathogenic fungi.
[0005] Agriculturally acceptable salts of the compounds of formula I comprise especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds I. Suitable cations are thus , in particular, alkali metal ions, preferably sodium and potassium, alkaline earth metals, preferably calcium, magnesium and barium, transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ions which, if desired, may carry one to four C1-C4 alkyl substituents and/or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, in addition, phosphonium ions, sulfonium ions, preferably tri(C1-C4 alkylsulfonium) , and sulfoxide ions, preferably tri(C1-C4 alkyl)sulfoxonium.
[0006] Acceptable acid addition salt anions are mainly chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-C4 alkanoic acids , preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound I with an acid of the corresponding anion, preferably from hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
[0007] The compounds of formula I can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers resulting from restricted rotation around a single bond of asymmetric groups and geometric isomers. They are also part of the subject matter of the present invention. A person skilled in the art will understand that a stereoisomer may be more active and/or may have beneficial effects when enriched in relation to the other stereoisomer(s) or when separated from the other stereoisomer(s) . Additionally, the person skilled in the art knows how to selectively separate, enrich and/or prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, for example a racemate, individual stereoisomers, or as an optically active form.
[0008] The compounds of formula I can be present in different crystal modifications, whose biological activity can be different. They are also part of the subject matter of the present invention.
[0009] With respect to the variables, the embodiments of the intermediates obtained during the preparation of the compounds I correspond to the embodiments of the compounds of formula I. The term "compounds I" refers to compounds of formula I.
[0010] In the definitions of the variables given above, collective terms are used that are generally representative for the substituents in question. The term "Cn-Cm" indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
[0011] Portions having two or more possibilities to be connected the following applies:
[0012] The moieties which do not have any parentheses in the name are linked through the last moiety, for example alkenyloxyimino C2-C6-C1C4 alkyl is linked via C1-C4 alkyl, heteroaryl-C1-C4 alkyl is linked via C1-alkyl C4, etc.
The moieties having parentheses in the name are bonded through the first moiety eg C(=O)-(C1-C6 alkyl) is bonded through C=O as indicated by the valence number of the carbon atom etc.
[0014] The term "halogen" refers to fluorine, chlorine, bromine and iodine.
[0015] The term "C1-C6 alkyl" refers to a straight or branched chain saturated hydrocarbon group having 1 to 6 carbon atoms, for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl.
[0016] The term "C1-C6 haloalkyl" refers to a straight or branched chain alkyl group having 1 to 6 carbon atoms (as defined above), in which some or all of the hydrogen atoms of these groups may be substituted. by halogen atoms as mentioned above, for example chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2, 2- difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl and pentafluoroethyl, 2- fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3, 3, 3-trichloropropyl, CH2-C2F5, CF2-C2F5, CF(CF3)2, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl) l)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl.
[0017] The term "C1-C6 alkoxy" refers to a straight or branched chain alkyl group having 1 to 6 carbon atoms (as defined above) that is attached via an oxygen, at any position on the alkyl group, for example methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy.
[0018] The term "halo C1-C6 alkoxy" refers to a C1-C6 alkoxy, as defined above, in which some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, for example, OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCL3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2, 2, 2-trifluoroethoxy, 2- chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3, 3-trifluoropropoxy, 3,3,3, 3-trichloropropoxy, OCH2-C2F5, OCF2- C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
[0019] The terms "phenyl-C1-C4 alkyl or heteroaryl-C1-C4 alkyl" refer to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a phenyl or heteroaryl radical, respectively.
The term "C1-C4 alkoxy-C1-C4 alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), in which one hydrogen atom of the alkyl radical is replaced by a C1 alkoxy group -C4 (as defined above). Likewise, the term "C1-C4 alkylthio-C1-C4 alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), in which one hydrogen atom of the alkyl radical is replaced by an alkylthio group. C1-C4.
The term "C1-C6 alkylthio" as used herein refers to straight or branched chain alkyl groups having 1 to 6 carbon atoms (as defined above) attached through a sulfur atom. Therefore, the term "C1-C6 haloalkylthio" as used herein refers to a straight or branched chain haloalkyl group having 1 to 6 carbon atoms (as defined above) attached through a sulfur atom in any position on the haloalkyl group.
The term "C1-C6 alkylsulfinyl" refers to straight or branched chain alkyl groups having 1 to 6 carbon atoms (as defined above) attached through an -S(=O)- moiety, in any position on the alkyl group, for example, methylsulfinyl and ethylsulfinyl and the like. Therefore, the term "C 1-C6 haloalkylsulfinyl" refers to a straight or branched chain haloalkyl group having 1 to 6 carbon atoms (as defined above), attached through an -S(=O)- moiety, in any position on the haloalkyl group.
[0023] The term "C1-C6 alkylsulfonyl" refers to straight or branched chain alkyl groups having 1 to 6 carbon atoms (as defined above), attached through an -S(=O)2- moiety, in any position on the alkyl group, for example methylsulfonyl. Therefore, the term "C1-C6 haloalkylsulfonyl" refers to a straight or branched chain haloalkyl group having 1 to 6 carbon atoms (as defined above), attached through an -S(=O)2-, moiety. at any position on the haloalkyl group.
[0024] The term "C1-C4 hydroxyalkyl" refers to alkyl having 1 to 4 carbon atoms, in which one hydrogen atom of the alkyl radical is replaced by an OH group.
[0025] The term "C1-C4 aminoalkyl" refers to alkyl having 1 to 4 carbon atoms, in which one hydrogen atom of the alkyl radical is replaced by an NH2 group.
[0026] The term "C1-C4 alkylamino-C1-C4 alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a C1 alkyl group -C4-NH-, which is bound through nitrogen. Likewise the term "dialkylamino C1-C4-C1-C4 alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by an (alkyl) group C1-C4)2N- which is bound through nitrogen.
[0027] The term "aminocarbonyl-C1-C4 alkyl" refers to alkyl having 1 to 4 carbon atoms, in which one hydrogen atom of the alkyl radical is replaced by a -(C=O)-NH2 group.
[0028] The term "C2-C6 alkenyl" refers to an unsaturated straight or branched chain hydrocarbon radical having 2 to 6 carbon atoms and a double bond at any position, such as ethenyl, 1-propenyl, 2-propenyl ( allyl) 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl.
[0029] The term "C2-C6 alkynyl" refers to an unsaturated straight or branched chain hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond, such as ethynyl, 1-propynyl, 2-propynyl ( propargyl) 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl.
The term "C3-C8 cycloalkyl" refers to saturated monocyclic hydrocarbon radicals with 3 to 8 carbon ring members, such as cyclopropyl (C3H5), cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
The term "C3-C8 cycloalkyloxy" refers to a cycloalkyl radical having 3 to 8 carbon atoms (as defined above), which is attached through an oxygen atom.
[0032] The term "C(=O)-(C1-C4)" refers to a radical that is bonded through the carbon atom of the C(=O) group, as indicated by the valence number of the atom. carbon.
[0033] The term "aliphatic" refers to compounds or radicals composed of carbon and hydrogen and which are non-aromatic compounds. An alicyclic compound or radical is an organic compound that is both aliphatic and cyclic. They contain one or more all-carbon rings that can be saturated or unsaturated, but have no aromatic character.
[0034] The terms "cyclic moiety" or "cyclic group" refer to a radical that is an alicyclic ring or an aromatic ring, such as, for example, phenyl or heteroaryl.
[0035] The term "and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R1a" refers to aliphatic groups, groups cyclics and groups, which contain an aliphatic and a cyclic moiety in a group, such as, for example, in phenyl-C1-C4 alkyl; therefore, a group that contains an aliphatic and a cyclic moiety, both of these moieties can be substituted or unsubstituted independently of each other.
[0036] The term "heteroaryl" refers to aromatic monocyclic or polycyclic ring systems, including in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S.
[0037] The term "phenyl" refers to aromatic ring systems including six carbon atoms (commonly referred to as benzene ring). In association with the A group, the term "phenyl" is to be interpreted as a benzene ring or phenylene ring, which is attached to both the oxadiazole moiety and the -CR3R4- group.
[0038] The term "saturated or partially unsaturated carbocycle with 3-, 4-, 5-, 6- or 7-membered" shall be understood in the sense of both saturated or partially unsaturated carbocycles with 3, 4, 5, 6 or 7 ring members. Examples include cyclopropyl, cyclopentyl, cyclopentenyl, cyclopentadienyl, cyclohexyl, cyclohexenyl, cyclohexadienyl, cycloheptyl, cycloheptenyl, cycloheptadienyl and the like.
[0039] The term "saturated, partially unsaturated, or mono- or bicyclic aromatic 3- to 10-membered heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include in addition to carbon atoms plus 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms" is to be understood to mean both mono- and bicyclic aromatic ring systems and also saturated and partially unsaturated heterocycles, eg: a saturated heterocycle with 3 or 4 members containing 1 or 2 heteroatoms of the group consisting of N, O and S as ring members such as oxirane, aziridine, thiyran, oxetane, azetidine, thiethane, [1,2]dioxetane, [1, 2]dithiethane, [ 1,2]diazetidine; is a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1, 2 or 3 heteroatoms from the group consisting of N, O and S as ring members such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2- tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl a, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1, 2, 4-oxadiazolidin-3-yl, 1, 2, 4-oxadiazolidin-5-yl, 1, 2, 4-thiadiazolidin-3-yl, 1, 2, 4-thiadiazolidin-5-yl, 1, 2, 4-triazolidin-3-yl, 1, 3, 4-oxadiazolidin-2-yl, 1, 3, 4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4- isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin- 5-ila , 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2 -isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3 -yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl -yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5 -yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2 -yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3 -yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3 -ila and also the corresponding -ylidene radicals; and a 7-membered saturated or partially unsaturated heterocycle such as tetra and hexahydroazepinyl such as 2, 3, 4,5-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5- , -6- or -7-yl, 3, 4, 5, 6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2, 3, 4, 7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 2, 3, 6, 7-tetrahydro[ 1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, hexahydroazepin-1-, -2-, -3- or -4-yl, tetra and hexahydrooxepinyl, such as 2, 3, 4,5-tetrahydro-[1H]-oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2, 3, 4, 7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2, 3, 6, 7-tetrahydro[1H]oxepin-2- , -3-, -4-, -5-, -6- or -7-yl, hexahydroazepin-1-, -2-, -3- or -4-yl, tetra and hexahydro-1,3-diazepinyl, tetra and hexahydro-1,4-diazepinyl, tetra and hexahydro-1,3-oxazepinyl, tetra and hexahydro-1,4-oxazepinyl, tetra and hexahydro-1,3-dioxepinyl, tetra and hexahydro-1,4-dioxepinyl and the corresponding radicals - ylidene; and the term "5- or 6-membered heteroaryl" or the term "5- or 6-membered heterocycloaromatic" refers to aromatic ring systems including in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms independently selected from the group which consists of N, O and S, for example a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol- 4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl ila, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1, 2, 4-triazolyl-1-yl, 1, 2, 4- triazol-3-yl, 1, 2, 4-triazol-5-yl, 1, 2, 4-oxadiazol-3-yl, 1, 2, 4-oxadiazol-5-yl and 1, 2, 4-thiadiazol- 3-yl, 1,2,4-thiadiazol-5-yl; or a 6-membered heteroaryl such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.
[0040] With respect to the variables, the embodiments of the intermediates correspond to the embodiments of the compounds I. Preference is given to the compounds I and, where applicable, also to the compounds of all the sub-formula given herein, in that all variables have independently of one another, or more preferably in combination (any possible combination of 2 or more substituents as defined herein) the following meanings:
[0041] In one aspect of the invention A is phenyl which is unsubstituted or substituted by 1, 2, 3 or 4 groups, identical or different, RA as defined or preferably as defined herein and wherein the group -C (R3R4)-NR1R2 is attached to the phenyl ring in the para position to the trifluoromethyloxadiazole group.
[0042] In one aspect of the invention A is phenyl which is unsubstituted or substituted by 1, 2, 3 or 4 groups, identical or different, RA as defined or preferably as defined herein and wherein the group -C (R3R4)-NR1R2 is attached to the phenyl ring in meta position to the trifluoromethyloxadiazole group.
[0043] In another aspect of the invention A is phenyl which is substituted by 1 or 2 identical or different groups, RA as defined or preferably as defined herein and wherein the group -C(R3R4)-NR1R2 is attached to the phenyl ring in the para position to the trifluoromethyloxadiazole group.
[0044] In another aspect of the invention A is phenyl which is unsubstituted and wherein the group -C(R3R4)-NR1R2 is attached to the phenyl ring in the para position relative to the trifluoromethyloxadiazole group.
[0045] In a preferred embodiment of the invention A is phenyl substituted by RA selected from halogen, or C1-C6 alkyl. In another preferred embodiment of the invention, A is phenyl substituted by halogen. In a special and preferred embodiment of the invention, A is phenyl substituted by F. In another special preferred embodiment of the invention, A is phenyl substituted by Cl.
[0046] In another preferred embodiment of the invention, A is phenyl substituted by C1-C6 alkyl. In a special preferred embodiment of the invention, A is phenyl substituted by CH3. In another special preferred embodiment of the invention, A is phenyl substituted by CH2CH3. In another special preferred embodiment of the invention, A is phenyl which is unsubstituted.
[0047] In one embodiment, A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include in addition to carbon atoms, 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocyclic ring is unsubstituted or substituted by 1 or 2 identical or different groups, RA as defined or preferably as defined herein.
[0048] In another embodiment, A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include, in addition to carbon atoms, 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocyclic ring is unsubstituted or substituted by 1 or 2 identical or different groups RA as defined or preferably as defined herein and wherein the group -C(R3R4)-NR1R2 is attached to the aromatic heterocycle with 6 members in the para position to the trifluoromethyloxadiazole group.
[0049] In another embodiment, A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include, in addition to carbon atoms, 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted or substituted by 1 or 2 identical or different groups RA as defined or preferably as defined herein and wherein the group -C(R3R4)-NR1R2 is attached to the 6-membered aromatic heterocycle in the meta position to the trifluoromethyloxadiazole group..
[0050] In another embodiment, A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include, in addition to carbon atoms, 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted or substituted by 1 or 2 identical or different groups RA as defined or preferably as defined herein and wherein the group -C(R3R4)-NR1R2 is attached to the aromatic heterocycle with 6 members in the ortho position to the trifluoromethyloxadiazole group.
[0051] In another embodiment, A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include, in addition to carbon atoms, 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted and wherein the group -C(R3R4)-NR1R2 is attached to the 6-membered aromatic heterocycle in the para position relative to the trifluoromethyloxadiazole group.
[0052] In another preferred embodiment, A is a 5-membered aromatic heterocycle, wherein the ring member atoms of the heterocycle include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N , O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 or 2 identical or different groups RA as defined or preferably defined herein.
[0053] In another preferred embodiment, A is a 5-membered aromatic heterocycle, wherein the ring member atoms of the heterocycle include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted.
[0054] In one embodiment, the invention relates to the use of compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof for combating harmful phytopathogenic fungi wherein the cyclic portion A is defined as in sub-formulas (A.1) to (A.12),
wherein #1 denotes the position which is attached to the trifluoromethyloxadiazole moiety and #2 denotes the position, which is attached to the -C(R3R4)-NR1R2 group of compounds of formula I; and wherein the cyclic moiety A is unsubstituted or substituted by 1 or 2 identical or different groups RA and wherein RA is as defined or preferably as defined herein. In another embodiment the cyclic moieties A as defined in any one of subformulas (A.1) to (A.12) is unsubstituted or substituted by 1 or 2 identical or different RA groups; and where RA is chlorine, fluorine or methyl. In a preferred embodiment, the cyclic portion A, as defined in any one of sub-formula (A.1) to (A.12), is unsubstituted.
[0055] In a preferred embodiment of the invention, RA is halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl or C3-C8 cycloalkyl; and wherein any of the aliphatic and cyclic moieties are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different RA groups, as defined or preferably as defined herein.
[0056] In another preferred embodiment of the invention, RA is halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl or C3-C8 cycloalkyl; and wherein any of the aliphatic and cyclic moieties are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different groups selected from halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy , and C3-C8 cycloalkyl; in particular fluorine.
[0057] More preferably RA is halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; in particular halogen, C1-C6 alkyl; more particularly RA is chlorine, fluorine or methyl. In a more preferred embodiment, RA is chlorine, fluorine or methyl.
[0058] RA according to the invention is halogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C1 haloalkylthio C6 or C3-C8 cycloalkyl. In a preferred embodiment of the invention, RA is halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, or C3-C8 cycloalkyl. Most preferably RA is halogen, in particular fluorine.
[0059] According to one embodiment R1 is H. According to one embodiment R1 is C1-C6 alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl. According to another embodiment R1 is C2-C6 alkenyl, preferably ethylene. According to another embodiment R1 is C2-C6 alkynyl, preferably ethynyl, 1-propynyl. According to another embodiment R1 is C3-C8 cycloalkyl, preferably cyclopropyl, cyclobutyl, cyclopentyl, in particular cyclopropyl, cyclopentyl or cyclohexyl.
[0060] According to one embodiment R1 represents C1-C6 alkyl substituted by halogen, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl. In a special embodiment of the invention R1 is CF3.
[0061] According to one embodiment R1 is C(=O)-(C1-C6 alkyl). According to one embodiment, R1 is C(=O)-(C1-C6 alkyl), wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t - butyl, in particular methyl, ethyl. According to one embodiment, R1 is C(=O)-(C1-C6 alkoxy), wherein alkoxy is preferably methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t- butoxy.
[0062] According to one embodiment R1 is phenyl-C1C4 alkyl, wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl , ethyl.
[0063] According to one embodiment R1 is heteroaryl-C1-C4 alkyl, wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in in particular methyl, ethyl and where heteroaryl is furan, thiophene, pyrazole, isoxazole, imidazole, oxazole, thiazole, triazole, oxidiazole, pyrol, pyriminine.
[0064] According to one embodiment R1 is phenyl. According to another embodiment R1 is benzyl. According to one embodiment R1 is naphthyl. According to one embodiment R 1 is 3- to 10-membered, saturated, partially unsaturated or mono- or bicyclic aromatic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include, in addition to carbon atoms, more 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 carbon ring member atoms of the heterocycle may be substituted by 1 or 2 groups independently selected from C (=O) and C(=S); and wherein the heteroaryl group in the heteroaryl-C1-C4 alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected a from N, O and S as ring member atoms especially furan, thiophene, pyrazole, isoxazole, imidazole, oxazole, thiazole, triazole, oxidiazole, pyrol, pyrimine.
[0065] According to another embodiment the aforementioned groups can carry one, two, three or four identical or different substituents selected from the group consisting of methyl, ethyl, propyl, butyl, preferably methyl. According to another embodiment the aforementioned groups can carry one, two, three or four identical or different substituents selected from the group consisting of methyl, ethyl, propyl, butyl, partially or fully halogenated, preferably partially methyl or fully halogenated, in particular CF3. According to another embodiment the aforementioned groups can carry one, two, three or four identical or different substituents selected from the group consisting of methoxy, ethoxy, propoxy, butoxy, preferably methoxy. According to another embodiment of the above the aforementioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of partially or fully halogenated methoxy, ethoxy, propoxy, butoxy, preferably methoxy partially or fully halogenated, in particular OCF3. In a special embodiment of the invention, R1 is phenyl. In another special embodiment of the invention, R1 is phenyl substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3. In another special embodiment of the invention, R1 is benzyl substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3. In another special embodiment R1 is naphthyl substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3. In another special embodiment of the invention, R1 is thiophene substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3. In another special embodiment of the invention, R1 is pyrol substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3. In another special embodiment of the invention, R1 is pyrazole substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3. In another special embodiment of the invention, R1 is pyrimidine substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3. In another special embodiment of the invention, R1 is oxidiazole substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3.
[0066] In a preferred embodiment R1 is H, C1C6 alkyl, C3-C6 cycloalkyl. In a special preferred embodiment R1 is H, CH3, cyclopropyl.
[0067] According to one embodiment R2 is H. According to one embodiment R2 is C1-C6 alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl , t-butyl, in particular methyl, ethyl. According to another embodiment R2 is C2-C6 alkenyl, preferably ethylene. According to another embodiment R2 is C2-C6 alkynyl, preferably ethynyl, 1-propynyl. According to another embodiment R2 is C3-C8 cycloalkyl, preferably cyclopropyl, cyclobutyl, cyclopentyl, in particular cyclopropyl, cyclopentyl or cyclohexyl.
[0068] According to one embodiment R2 is C1-C6 alkyl substituted by halogen, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl. In a special embodiment of the invention, R2 is CF3.
[0069] According to one embodiment R2 is C(=O)-(C1-C6 alkyl). According to one embodiment R2 is C(=O)-(C1-C6 alkyl), wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t- butyl in particular methyl, ethyl. According to one embodiment of R2 is C(=O)-(C1-C6 alkoxy), wherein the alkoxy is preferably methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy.
[0070] According to one embodiment R2 is phenyl-C1-C4 alkyl, wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particularly methyl, ethyl.
[0071] According to one embodiment R2 is heteroaryl-C1-C4 alkyl, wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particularly methyl, ethyl and wherein the heteroaryl is furan, thiophene, pyrazole, isoxazole, imidazole, oxazole, thiazole, triazole, oxidiazole, pyrol, pyriminine.
[0072] According to one embodiment R2 is phenyl. According to another embodiment R2 is a benzyl group. According to one embodiment R2 is naphthyl. According to one embodiment R2 is a 3- to 10-membered, saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include, in addition to carbon atoms, plus 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 of the carbon ring member atoms of the heterocycle may be substituted by 1 or 2 groups independently selected from of C(=O) and C(=S); and wherein the heteroaryl group in the heteroaryl-C1-C4 alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include, in addition to carbon atoms, 1, 2, 3 or 4 selected heteroatoms from N, O and S as ring member atoms especially furan, thiophene, pyrazole, isoxazole, imidazole, oxazole, thiazole, triazole, oxidiazole, pyrol, pyrimidine.
[0073] According to another embodiment the aforementioned groups can carry one, two, three or four identical or different substituents selected from the group consisting of methyl, ethyl, propyl, butyl, preferably methyl. According to another embodiment the aforementioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of methyl, ethyl, propyl, butyl, partially or fully halogenated, preferably partially methyl or fully halogenated, in particular CF3. According to another embodiment the aforementioned groups can carry one, two, three or four identical or different substituents selected from the group consisting of methoxy, ethoxy, propoxy, butoxy, preferably methoxy. According to another embodiment the aforementioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of partially or fully halogenated methoxy, ethoxy, propoxy, butoxy, preferably partially methoxy or fully halogenated in particular OCF3. In a special embodiment of the invention, R2 is phenyl. In another special embodiment of the invention, R2 is a phenyl group substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3. In another special embodiment of the invention, R2 is a benzyl group substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3. In another special embodiment R2 is naphthyl substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3. In another special embodiment of the invention, R2 is thiophene substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3. In another special embodiment of the invention, R2 is pyrol substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3. In another special embodiment of the invention, R2 is pyrazole substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3. In another special embodiment of the invention, R2 is pyrimidines substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3. In another special embodiment of the invention, R2 is oxydiazole substituted by Cl, F, Br, I, CH3, OCH3, CF3 or OCF3.
[0074] In another preferred embodiment, R2 is H, C1-C6 alkyl, C2-C6 alkenyl, C1-C6 alkynyl, C3-C6 cycloalkyl, phenyl-C1-C4 alkyl, heteroaryl-C1-C4 alkyl, phenyl. In a special preferred embodiment R2 is H, C1-C6 alkyl, C3-C6 cycloalkyl, phenyl-C1-C4 alkyl, heteroaryl-C1C4 alkyl, phenyl. In another special preferred embodiment R2 is H, C1-C6 alkyl, C3-C6 cycloalkyl, phenyl-C1-C4 alkyl, phenyl. In another special preferred embodiment R2 is H, CH3, CH2CH3, cyclopropyl, phenyl, benzyl.
[0075] In another preferred embodiment R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, phenyl-C1-C4 alkyl, heteroaryl-C1 alkyl -C4, phenyl or a saturated, partially unsaturated 3- to 10-membered mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include, in addition to carbon atoms, 1, 2, 3 or more 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 of the carbon ring member atoms of the heterocycle may be substituted by 1 or 2 groups independently selected from C(=O) and C (=S); and wherein the heteroaryl group in the heteroaryl-C1-C4 alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include, in addition to carbon atoms, 1, 2, 3 or 4 selected heteroatoms from N, O and S as ring member atoms; and wherein any of the aforementioned aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different R1a groups; wherein R1a is halogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkyl, NHSO2 -C1-C4 alkyl, (C=O)-(C1-C4 alkyl)C(=O)-(C1-C4 alkoxy) or C1-C6 alkylsulfonyl; and wherein R2 is C(=O)-(C1-C6 alkyl) or C(=O)-(C1-C6 alkoxy).
[0076] In another embodiment R1 and R2 independently of one another are hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C(=O)-(C1-C6 alkyl ), C(=O)-(C1-C6 alkoxy), phenyl-C1-C4 alkyl or phenyl; and wherein the aliphatic and cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different R 1a groups as defined herein.
[0077] In another embodiment R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl and R2 is hydrogen, C1-C6 alkyl, C2C6 alkenyl or C2-C6 alkynyl, C3-C8 cycloalkyl, phenyl -C1-C4 alkyl, heteroaryl-C1C4 alkyl, phenyl or heteroaryl; and wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle, wherein the ring includes, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms ; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different R1a groups; wherein R1a is defined or preferably as defined herein.
[0078] In one aspect of the invention, R1 and R2 independently of one another are hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C(=O)-(C1-C6 alkyl ) or C(=O)-(C1-C6 alkoxy); and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different R 1a groups as defined or preferably as defined herein.
[0079] In another embodiment R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C8 cycloalkyl and R2 is C(=O)-(C1C6 alkyl), C(=O) -(C1-C6 alkoxy); and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different R 1a groups as defined or preferably as defined herein.
[0080] In another embodiment R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C8 cycloalkyl and R2 is C(=O)-(C1-C6 alkyl); and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the fluorine, chlorine and methyl group.
[0081] In one aspect of the invention, R1 and R2 independently of one another are hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C8 cycloalkyl; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different R 1a groups as defined or preferably as defined herein.
[0082] In another embodiment R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl and R2 is phenyl-C1-C4 alkyl, heteroaryl-C1C4 alkyl, phenyl or heteroaryl; and wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle, wherein the ring includes, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms ; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different groups of R 1a as defined or preferably as defined herein.
[0083] In another aspect of the invention, R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl and R2 is phenyl-C1-C4 alkyl, heteroaryl-C1-C4 alkyl or phenyl; and wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle, wherein the ring includes in addition to carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different groups of R 1a as defined or preferably as defined herein.
[0084] In one embodiment R1 is hydrogen or C1-C6 alkyl and R2 is C3-C8 cycloalkyl; and wherein the cycloalkyl group is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably as defined herein.
[0085] In one embodiment R1 is hydrogen or C1-C6 alkyl and R2 is C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, wherein the aliphatic groups are unsubstituted or carry 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably as defined herein.
[0086] In one embodiment R1 is hydrogen or C1-C6 alkyl and R2 is phenyl, a 5- to 6-membered aromatic heterocycle, phenyl-C1-C4 alkyl or heteroaryl-C1-C4 alkyl, wherein the member atoms of the heterocyclic ring ring include, in addition to carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably as defined herein.
[0087] In one embodiment R1 is hydrogen or C1-C6 alkyl and R2 is phenyl-C1-C4 alkyl or heteroaryl-C1-C4 alkyl; wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different R 1a groups as defined or preferably as defined herein.
[0088] In one embodiment R1 is hydrogen or C1-C6 alkyl and R2 is phenyl or a 5- to 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably as defined herein.
[0089] In one embodiment of the invention, R1 and R2 together with the nitrogen atom to which they are attached form a saturated or partially unsaturated mono- or bicyclic 3- to 7-membered heterocycle, wherein the heterocycle includes, in addition to a nitrogen atom and one or more carbon atoms, 1, 2 or 3 heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=O) and C(=S); and wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different R1a groups; wherein R1a is halogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkyl, NHSO2 -C1-C4 alkyl, (C=O)-C1-C4 alkyl, C(=O)-C1-C4 alkoxy or C1-C6 alkylsulfonyl.
[0090] In one embodiment of the invention, R1 and R2 together with the N atom to which it is attached form a saturated or partially unsaturated heterocycle with 3 to 6 members, wherein the heterocycle includes, in addition to a N atom. nitrogen and one or more carbon atoms, no other additional heteroatoms.
[0091] In one embodiment of the invention, R1 and R2 together with the N to which they are attached form a saturated or partially unsaturated 3- to 6-membered heterocycle, in which one or two CH2 groups of the heterocycle may be substituted by one or two groups independently selected from the group of C(=O) and C(=S). In one embodiment R1 and R2 together with the nitrogen atom to which they are attached form a 5- to 7-membered saturated or partially unsaturated monocyclic heterocycle, wherein the heterocycle includes in addition to a nitrogen atom and one or more atoms carbon, no additional heteroatoms or 1 or 2 heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=O) and C(=S); and wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably as defined herein; particularly R1a is halogen or C1-C6 alkyl.
[0092] In another embodiment R1 and R2 together with the nitrogen atom to which they are attached form a 5- to 6-membered saturated or partially unsaturated monocyclic heterocycle, wherein the heterocycle includes, in addition to a nitrogen atom and one or more carbon atoms, no additional heteroatom or 1 other heteroatom independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=O) and C(=S); and wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably as defined herein; particularly R1a is halogen or C1-C6 alkyl.
[0093] In one embodiment, the invention R1a is halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy. In another preferred aspect of the invention, R1a is fluorine, chlorine, cyano, methyl, methoxy, trifluoromethyl, trifluoromethoxy, difluoromethyl or difluoromethoxy. In a more preferred aspect of the invention, R1a is halogen or C1-C6 alkyl; particularly fluorine, chlorine or methyl.
[0094] In a special preferred embodiment of the invention, R1 and R2 together with the N atom to which they are attached form an aziridinyl.
[0095] In a special preferred embodiment of the invention, R1 and R2 together with the N atom to which they are attached form an azetidinyl.
[0096] In a special preferred embodiment of the invention, R1 and R2 together with the N atom to which they are attached form a 1-pyrrolidinyl.
[0097] In a special preferred embodiment of the invention, R1 and R2 together with the N atom to which they are attached form a 1-piperidinyl.
[0098] In a special preferred embodiment of the invention, R1 and R2 together with the N atom to which they are attached form a 1-piperazinyl.
[0099] In a special preferred embodiment of the invention, R1 and R2 together with the N atom to which they are attached form a 1-methyl-4-piperazinyl.
[0100] In a special preferred embodiment of the invention, R1 and R2 together with the N atom to which they are attached form a 4-morpholinyl.
[0101] In one embodiment, the invention R1a is halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy. In another preferred aspect of the invention, R1a is fluorine, chlorine, cyano, methyl, methoxy, trifluoromethyl, trifluoromethoxy, difluoromethyl or difluoromethoxy. In a more preferred aspect of the invention, R1a is halogen or C1-C6 alkyl; particularly fluorine, chlorine or methyl.
[0102] According to one embodiment R3 is H. According to one embodiment R3 is C1-C6 alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
[0103] According to one embodiment R3 is C1C6 haloalkyl, preferably by methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, substituted with halogen, in particular methyl, ethyl. In a preferred embodiment of the invention, R3 is H, CH3 and CF3. In a special embodiment of the invention, R3 is CF3.
[0104] According to one embodiment R4 is H. According to one embodiment R4 is C1-C6 alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
[0105] According to one embodiment R4 is C1C6 haloalkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, substituted with halogen, in particular methyl, ethyl . In a preferred embodiment of the invention, R4 is H, CH3 and CF3. In a special embodiment of the invention, R4 is CF3.
[0106] According to an embodiment R3 and R4 are, independently of each other, hydrogen, fluorine, methyl or trifluoromethyl. In another embodiment R3 and R4 are independently selected from the group consisting of hydrogen and C1-C4 alkyl, in particular from between hydrogen and CH3. According to another embodiment R3 is hydrogen and R4 is hydrogen or C1-C4 alkyl, in particular hydrogen or CH3.
[0107] In another aspect R3 and R4 are both hydrogens. In another aspect R3 is hydrogen and R4 is CH3. In yet another aspect R3 is hydrogen and R4 is trifluoromethyl. In yet another aspect R3 and R4 are both methyl. In one embodiment R3 and R4 are both trifluoromethyl.
[0108] In yet another embodiment R3 and R4 independently of each other are H, CH3 or trifluoromethyl.
[0109] In one embodiment, the present invention relates to compounds (I.1) of the formula I wherein: A is phenyl or a 5- or 6-membered aromatic heterocycle wherein the ring member atoms of the heterocyclic ring include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1, 2, 3 or 4 identical or different groups Ra; where RA is halogen, cyano, NO2, OH, NH2, SH, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C6 alkenyl, C2-C6 alkynyl, cycloalkyl C3-C8 or C3-C8 cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1, 2, 3 or 4 identical or different Ra groups; wherein Ra is halogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1C6 haloalkylthio or C3-C8 cycloalkyl; R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, phenyl-C1-C4 alkyl, heteroaryl-C1C4 alkyl, phenyl, naphthyl or a saturated, partially unsaturated or heterocycle 3- to 10-membered mono- or bicyclic aromatic, wherein the ring member atoms of said mono- or bicyclic heterocycle include, in addition to carbon atoms, a further 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 carbon ring member atoms of the heterocycle may be substituted by 1 or 2 groups selected independently from C(=O) and C(=S); and wherein the heteroaryl group in the heteroaryl-C1-C4 alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include, in addition to carbon atoms, 1, 2, 3 or 4 selected heteroatoms from N, O and S as ring member atoms; and wherein any of the aforementioned aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R1a ; wherein R1a is halogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1C6 haloalkylthio, C3-C8 cycloalkyl, NHSO2-C1-C4 alkyl, (C=O)-C1-C4 alkyl , C(=O)-C1-C4 alkoxy, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl;R2 is C(=O)-(C1-C6 alkyl), C(=O)-(C1-C6 alkoxy); or R1 and R2 together with the nitrogen atom to which they are attached form a saturated or partially unsaturated 3- to 7-membered mono- or bicyclic heterocycle, wherein the heterocycle includes, in addition to a nitrogen atom and one or more atoms carbon, no other heteroatoms, or 1, 2 or 3 other heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=O) and C(=S); and wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably as defined herein; R 3 is H, C 1 -C 4 alkyl or C 1 -haloalkyl C4;R4 is H, C1-C4 alkyl or C1-C4 haloalkyl; or the N-oxides, or the agriculturally acceptable salts thereof.
[0110] In another embodiment, the invention relates to compounds (I.1), wherein A is (A.2). In another embodiment, the invention relates to compounds (I.1), wherein A is (A.2), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.1), wherein A is (A.2) and wherein A is unsubstituted.
[0111] In another embodiment, the invention relates to compounds (I.1), wherein A is (A.8). In another embodiment, the invention relates to compounds (I.1), wherein A is (A.8), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.1), wherein A is (A.8) and wherein A is unsubstituted.
[0112] In another embodiment, the invention relates to compounds (I.1), wherein A is (A.4). In another embodiment, the invention relates to compounds (I.1), wherein A is (A.4), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.1), wherein A is (A.4) and wherein A is unsubstituted.
[0113] In one embodiment, the present invention relates to compounds (I.2) of the formula I wherein: A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1, 2, 3 or 4 identical or different groups Ra; where RA is halogen, cyano, NO2, OH, NH2, SH, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C6 alkenyl, C2-C6 alkynyl, cycloalkyl C3-C8 or C3-C8 cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1, 2, 3 or 4 identical or different Ra groups; wherein Ra is halogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1C6 haloalkylthio or C3-C8 cycloalkyl; R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, phenyl-C1-C4 alkyl, heteroaryl-C1C4 alkyl, phenyl or a saturated, partially unsaturated or mono aromatic heterocycle - or bicyclic with 3 to 10 members, wherein the ring member atoms of said mono- or bicyclic heterocycle include, in addition to carbon atoms, further 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 ring member atoms of the heterocycle carbon may be substituted by 1 or 2 groups independently selected from C(=O) and C(=S); and wherein the heteroaryl group in the heteroaryl-C1-C4 alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include, in addition to carbon atoms, 1, 2, 3 or 4 selected heteroatoms from N, O and S as ring member atoms; and wherein any of the aforementioned aliphatic or cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R1a ; wherein R1a is halogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl,C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1C6 haloalkylthio, C3-C8 cycloalkyl, NHSO2-C1-C4 alkyl, (C=O)-C1-C4 alkyl , C(=O)-C1-C4 alkoxy, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl;R2 is C(=O)-(C1-C6 alkyl), C(=O)-(C1-C6 alkoxy); or R1 and R2 together with the nitrogen atom to which they are attached form a 5- to 7-membered saturated or partially unsaturated monocyclic heterocycle, wherein the heterocycle includes, in addition to a nitrogen atom and one or more carbon atoms, no other heteroatoms or 1, 2 or 3 other heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=O) and C(=S); and wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably as defined herein; particularly R 1a is halogen or C 1 -C 6 alkyl; R 3 , R 4 independently of one another are hydrogen C 1 C 4 alkyl or halo C 1 -C 4 alkyl; or the N-oxides, or the agriculturally acceptable salts thereof.
[0114] In another embodiment, the invention relates to compounds (I.2), wherein A is (A.2). In another embodiment, the invention relates to compounds (I.2), wherein A is (A.2), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.2), wherein A is (A.2) and wherein A is unsubstituted.
[0115] In another embodiment, the invention relates to compounds (I.2), wherein A is (A.8). In another embodiment, the invention relates to compounds (I.2), wherein A is (A.8), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.2), wherein A is (A.8) and wherein A is unsubstituted.
[0116] In another embodiment, the invention relates to compounds (I.2), wherein A is (A.4). In another embodiment, the invention relates to compounds (I.2), wherein A is (A.4), and wherein R4 is hydrogen or CH3. In another embodiment, the invention relates to compounds (I.2), wherein A is (A.4), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.2), wherein A is (A.4), and wherein A is substituted by an RA group as defined or preferably as defined herein and where R3 is hydrogen and R4 is hydrogen or CH3. In yet another embodiment, the invention relates to compounds (I.2), wherein A is (A.4) and wherein A is unsubstituted. In yet another embodiment, the invention relates to compounds (I.2), wherein A is (A.4) and wherein A is unsubstituted and wherein R3 is hydrogen and wherein R4 is hydrogen or CH3.
[0117] In one embodiment, the present invention relates to compounds (I.3) of the formula I wherein: A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1, 2, 3 or 4 identical or different groups Ra; where RA is halogen, cyano, NO2, OH, NH2, SH, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C6 alkenyl, C2-C6 alkynyl, cycloalkyl C3-C8 or C3-C8 cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1, 2, 3 or 4 identical or different Ra groups; wherein Ra is halogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1C6 haloalkylthio or C3-C8 cycloalkyl; R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynylor C3-C6 cycloalkyl, R2 is C(=O)-(C1-C6 alkyl), C(=O)-(C1-C6 alkoxy); R3 is hydrogen; R4 is hydrogen, C1-C4 alkyl or C1-C4 haloalkyl; or the N-oxides, or the agriculturally acceptable salts thereof.
[0118] In another embodiment, the invention relates to compounds (I.3), wherein A is (A.2). In another embodiment, the invention relates to compounds (I.3), wherein A is (A.2), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.3), wherein A is (A.2) and wherein A is unsubstituted.
[0119] In another embodiment, the invention relates to compounds (I.3), wherein A is (A.8). In another embodiment, the invention relates to compounds (I.3), wherein A is (A.8), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.3), wherein A is (A.8) and wherein A is unsubstituted.
[0120] In another embodiment, the invention relates to compounds (I.3), wherein A is (A.4). In another embodiment, the invention relates to compounds (I.3), wherein A is (A.4), and wherein R4 is hydrogen or CH3. In another embodiment, the invention relates to compounds (I.3), wherein A is (A.4), and wherein A is substituted by an RA group as defined or preferably as defined herein. In another embodiment, the invention relates to compounds (I.3), wherein A is (A.4), and wherein A is substituted by an RA group as defined or preferably as defined herein , and where R4 is hydrogen or CH3. In yet another embodiment, the invention relates to compounds (I.3), wherein A is (A.4) and wherein A is unsubstituted. In yet another embodiment, the invention relates to compounds (I.3), wherein A is (A.4), and wherein A is unsubstituted, and wherein R4 is hydrogen or CH3.
[0121] In one embodiment, the present invention relates to compounds (I.4) of the formula I wherein: A is phenyl or a 5- or 6-membered aromatic heterocycle wherein the ring member atoms of the heterocyclic ring include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1, 2, 3 or 4 identical or different groups Ra; where RA is chlorine, fluorine or methyl; R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6R2 cycloalkyl is C(=O)-(C1-C6 alkyl), C(=O) -(C1-C6 alkoxy);R3 is hydrogen;R4 is hydrogen or CH3;or the N-oxides, or the agriculturally acceptable salts thereof.
[0122] In another embodiment, the invention relates to compounds (I.4), wherein A is (A.2). In another embodiment, the invention relates to compounds (I.4) wherein A is (A.2), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.4), wherein A is (A.2) and wherein A is unsubstituted.
[0123] In another embodiment, the invention relates to compounds (I.4), wherein A is (A.8). In another embodiment, the invention relates to compounds (I.4) wherein A is (A.8), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.4), wherein A is (A.8) and wherein A is unsubstituted.
[0124] In another embodiment, the invention relates to compounds (I.4), wherein A is (A.4). In another embodiment, the invention relates to compounds (I.4) wherein A is (A.4), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.4), wherein A is (A.4) and wherein A is unsubstituted.
[0125] In one embodiment, the present invention relates to compounds (I.5) of the formula I wherein: A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1, 2, 3 or 4 identical or different groups Ra; where RA is halogen, cyano, NO2, OH, NH2, SH, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C6 alkenyl, C2-C6 alkynyl, cycloalkyl C3-C8 or C3-C8 cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1, 2, 3 or 4 identical or different Ra groups; wherein Ra is halogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1C6 haloalkylthio or C3-C8 cycloalkyl;R1 and R2 together with the nitrogen atom to which they are attached form a 5- to 7-membered saturated or partially unsaturated monocyclic heterocycle, wherein the heterocycle includes, in addition to a nitrogen atom and one or more carbon atoms, no other heteroatoms. or 1, 2 or 3 other heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle are replaced by one or two groups independently selected from the group of C(=O) and C(=S); and wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably as defined herein; particularly R 1a is halogen or C 1 -C 6 alkyl; R 3 , R 4 independently of one another are hydrogen C 1 C 4 alkyl or halo C 1 -C 4 alkyl; or the N-oxides, or the agriculturally acceptable salts thereof.
[0126] In another embodiment, the invention relates to compounds (I.5), wherein A is (A.2). In another embodiment, the invention relates to compounds (I.5) wherein A is (A.2), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.5), wherein A is (A.2) and wherein A is unsubstituted.
[0127] In another embodiment, the invention relates to compounds (I.5), wherein A is (A.8). In another embodiment, the invention relates to compounds (I.5) wherein A is (A.8), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.5), wherein A is (A.8) and wherein A is unsubstituted.
[0128] In another embodiment, the invention relates to compounds (I.5), wherein A is (A.4). In another embodiment, the invention relates to compounds (I.5), wherein A is (A.4), and wherein R4 is hydrogen or CH3. In another embodiment, the invention relates to compounds (I.5) wherein A is (A.4), and wherein A is substituted by an RA group as defined or preferably as defined herein. In another embodiment, the invention relates to compounds (I.5), wherein A is (A.4), and wherein A is substituted by an RA group as defined or preferably as defined herein , and where R3 is hydrogen and R4 is hydrogen or CH3. In yet another embodiment, the invention relates to compounds (I.5), wherein A is (A.4) and wherein A is unsubstituted. In yet another embodiment, the invention relates to compounds (I.5), wherein A is (A.4), and wherein A is unsubstituted and wherein R3 is hydrogen and wherein R4 is hydrogen or CH3.
[0129] In one embodiment, the present invention relates to compounds (I.6) of the formula I wherein: A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1, 2, 3 or 4 identical or different groups Ra; where RA is halogen, cyano, NO2, OH, NH2, SH, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C6 alkenyl, C2-C6 alkynyl, cycloalkyl C3-C8 or C3-C8 cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1, 2, 3 or 4 identical or different Ra groups; wherein Ra is halogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1C6 haloalkylthio or C3-C8 cycloalkyl;R1 and R2 together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated or partially unsaturated monocyclic heterocycle, wherein the heterocycle includes, in addition to a nitrogen atom and one or more carbon atoms, no other heteroatoms or 1 other heteroatom independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=O) and C(=S); and wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably as defined herein; particularly R1a is halogen or C1-C6 alkyl;R3 is hydrogen;R4 is hydrogen, C1-C4 alkyl or C1-C4 haloalkyl; or the N-oxides, or the agriculturally acceptable salts thereof.
[0130] In another embodiment, the invention relates to compounds (I.6), wherein A is (A.2). In another embodiment, the invention relates to compounds (I.6), wherein A is (A.2), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.6), wherein A is (A.2) and wherein A is unsubstituted.
[0131] In another embodiment, the invention relates to compounds (I.6), wherein A is (A.8). In another embodiment, the invention relates to compounds (I.6), wherein A is (A.8), and wherein A is substituted by an RA group as defined or preferably as defined herein. In yet another embodiment, the invention relates to compounds (I.6), wherein A is (A.8) and wherein A is unsubstituted.
[0132] In another embodiment, the invention relates to compounds (I.6), wherein A is (A.4). In another embodiment, the invention relates to compounds (I.6), wherein A is (A.4), and wherein R4 is hydrogen or CH3. In another embodiment, the invention relates to compounds (I.6), wherein A is (A.4), and wherein A is substituted by an RA group as defined or preferably as defined herein. In another embodiment, the invention relates to compounds (I.6), wherein A is (A.4), and wherein A is substituted by an RA group as defined or preferably as defined herein , and where R4 is hydrogen or CH3. In yet another embodiment, the invention relates to compounds (I.6), wherein A is (A.4) and wherein A is unsubstituted. In yet another embodiment, the invention relates to compounds (I.6), wherein A is (A.4), and wherein A is unsubstituted, and wherein R4 is hydrogen or CH3.
[0133] According to one embodiment, the present invention relates to compounds of the formula IA
or the use of formula IA compounds to control phytopathogenic fungi. Here, the variables are as defined elsewhere in this description for formula I, or as defined as being preferred for formula I.
[0134] According to one embodiment, the present invention relates to compounds of the formula IB
or the use of formula IB compounds to control phytopathogenic fungi. Here, the variables are as defined elsewhere in this description for formula I, or as defined as being preferred for formula I.
[0135] According to one embodiment, the present invention relates to compounds of the formula IC
or the use of compounds of formula IC to control phytopathogenic fungi. Here, the variables are as defined elsewhere in this description for formula I, or as defined as being preferred for formula I.
[0136] According to one embodiment, the present invention relates to compounds of formula ID
or the use of compounds of formula ID to control phytopathogenic fungi. Here, the variables are as defined elsewhere in this description for formula I, or as defined as being preferred for formula I.
[0137] According to one embodiment, the present invention relates to compounds of the formula IE
or the use of compounds of the formula IE for the control of phytopathogenic fungi. Here, the variables are as defined elsewhere in this description for formula I, or as defined as being preferred for formula I.
[0138] According to one embodiment, the present invention relates to compounds of the formula IF
or the use of compounds of formula IF to control phytopathogenic fungi. Here, the variables are as defined elsewhere in this description for formula I, or as defined as being preferred for formula I.
[0139] According to one embodiment, the present invention relates to compounds of the formula IG
or the use of formula IG compounds for the control of phytopathogenic fungi. Here, the variables are as defined elsewhere in this description for formula I, or as defined as being preferred for formula I.
[0140] According to one embodiment, the present invention relates to compounds of the formula IH
or the use of compounds of the formula IH for the control of phytopathogenic fungi. Here, the variables are as defined elsewhere in this description for formula I, or as defined as being preferred for formula I.
[0141] According to one embodiment, the present invention relates to compounds of formula II
or to the use of the compounds of formula I for the control of phytopathogenic fungi. Here, the variables are as defined elsewhere in this description for formula I, or as defined as being preferred for formula I.
[0142] According to one embodiment, the present invention relates to compounds of the formula IJ or the use of compounds of the formula IJ for the control of phytopathogenic fungi. Here, the variables are as defined elsewhere in this description for formula I, or as defined as being preferred for formula I.

[0143] According to one embodiment, the present invention relates to compounds of the formula IK, IL, IM, IN, IO, IP, IQ, IR or IS or to the use of compounds of the formula IK, IL, IM , IN, IO, IP, IQ, IR or IS for the control of phytopathogenic fungi. Here, the variables R3 and R4 are as defined or preferably as defined herein for formula I.


[0144] Preference is given to compounds I, used according to the invention, and compounds according to the invention compiled in Tables 1 to 10 below. With regard to the compounds according to the invention, the exception as defined above will be considered. The groups mentioned for a substituent in the tables are furthermore per se, irrespective of the combination in which they are mentioned, a particularly preferred aspect of the substituent in question.- Table 1:
[0145] The compounds of the formula I.A, in which R1 and R2 for each individual compound, correspond in each case to a line in Table A (I.A.A-1 to I.A.A-973). For example, the compound of IAA-3 is therefore to be understood as a compound of formula IA, wherein the meaning of R1 and R2 is as defined in row A-3 of Table A (R1 is hydrogen and R2 is ethyl).- Table 2
[0146] The compounds of the formula I.B, in which R1 and R2 for each individual compound, correspond in each case to a line in Table A (I.B.A-1 to I.B.A-973).- Table 3:
[0147] The compounds of the formula I.C, in which R1 and R2 for each individual compound, correspond in each case to a line in Table A (I.C.A-1 to I.C.A-973)- Table 4:
[0148] The compounds of the formula I.D, in which R1 and R2 for each individual compound, correspond in each case to a line in Table A (I.D.A-1 to I.D.A-973).- Table 5:
[0149] The compounds of the formula I.E, in which R1 and R2 for each individual compound, correspond in each case to a line in Table A (I.E.A-1 to I.E.A-973).- Table 6:
[0150] The compounds of the formula I.F, wherein R1 and R2 for each individual compound, correspond in each case to a line in Table A (I.F.A-1 to I.F.A-973).- Table 7:
[0151] The compounds of the formula I.G, in which R1 and R2 for each individual compound, correspond in each case to a line in Table A (I.G.A-1 to I.G.A-503).- Table 8:
[0152] The compounds of the formula I.H, in which R1 and R2 for each individual compound, correspond in each case to a line in Table A (I.H.A-1 to I.H.A-973).- Table 9:
The compounds of the formula I.I, in which R1 and R2 for each individual compound, correspond in each case to a line in Table A (I.I.A-1 to I.I.A-973).- Table 10:
[0154] The compounds of the formula IJ, where R1 and R2 for each individual compound, correspond in each case to a line in Table A (IJA-1 to IJA-973).








[0155] The compounds of formula I can be prepared according to methods or in analogy to methods that are described in the state of the art. The synthesis takes advantage of starting materials that are commercially available or can be prepared according to conventional procedures starting from readily available compounds. For example, compounds of formula I can be prepared by reacting type II amidines with trifluoroacetic anhydride in an organic solvent, preferably an ethereal solvent at temperatures between 0 °C and 100 °C, preferably at room temperature, as previously described in WO2013 /008162.

[0156] A person skilled in the art will recognize that type II compounds can be accessed by treating type III nitriles with hydroxylamine (or its HCl salt) in an organic solvent and in the presence of a base (for prior art see for example WO 2009/074950, WO 2006/013104, EP 1 932 843).

[0157] Compounds III can be prepared by reacting the type IV carbonyl compound with the respective amine in an organic solvent and in the presence of a base, followed by subsequent treatment of the intermediate iminium species V with an organometallic reagent or hydride (if R4 =H). If appropriate, the iminium species V can be isolated. The reaction is preferably carried out in an ethereal solvent and at temperatures between -78 °C and 40 °C, more preferably at -15 °C or at room temperature as previously described (see, for example, Tetrahedron Letters 52(2), 281- 284 2011 or Journal

[0158] Compounds IV are either commercially available or can be accessed through known methods that are obvious to one skilled in the art.
The compounds of the formula I or compositions comprising said compounds according to the invention and mixtures comprising said compounds and compositions respectively, are suitable as fungicides. They are distinguished by excellent efficacy against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which are specially derived from the following classes or are closely related to any of them: Ascomycota (Ascomycetes) for example, but not limited to the genera Cocholiobolus, Colletotrichum, Fusarium, Microdochium, Penicillium, Phoma, Magnaporte, Zymoseptoria and Pseudocercosporella; Basdiomycota (Basidiomycetes) for example, but not limited to Phakospora, Puccinia, Rhizoctonia, Sphacelotheca, Tilletia, Typhula and Ustilago genera; Chytridiomycota (Chitridiomycetes) for example, but not limited to the genera Chytridiales and Synchytrium; Deuteromycetes (syn. Fungi imperfecti), for example, but not limited to the genera Ascochyta, Diplodia, Erysiphe, Fusarium, Phomopsis and Pyrenophora; Peronosporomycetes (syn. Oomycetes), for example but not limited to the genus Peronospora, Pythium, Phytophthora; Plasmodiophoromycetes eg but not limited to the genus Plasmodiophora; Zygomycetes for example, but not limited to the genus Rhizopus.
[0160] Some of the compounds of the formula I and the compositions according to the invention are systemically effective and can be used in crop protection as foliar fungicides, seed coating fungicides and soil fungicides. Furthermore, they are suitable for controlling harmful fungi, which occur in particular in wood or plant roots.
[0161] The compounds I and the compositions according to the invention are particularly important in the control of a multiplicity of phytopathogenic fungi in various cultivated plants, such as cereals, for example wheat, rye, barley, triticale, oats or rice; sugar beet, for example sugar beet or fodder beet; fruits, such as pomoids, stone fruits or soft fruits, for example apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or currants; leguminous plants such as lentils, peas, alfalfa or soybeans; oil plants, such as rapeseed, mustard, olives, sunflowers, coconut, cocoa, castor plants, oil palms, peanuts or soybeans; cucurbits such as pumpkins, cucumbers or melons; fibrous plants such as cotton, flax, hemp or jute; citrus fruits such as oranges, lemons, grapefruit or tangerines; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants such as avocados, cinnamon or camphor; energy plants and raw materials such as corn, soybeans, canola, sugar cane or palm oil; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape vines); hop; peat; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants such as flowers, shrubs, broad-leaved or evergreen trees, for example conifers; and in plant propagation material, such as seeds, and the harvest material of these plants.
[0162] Preferably, the compounds I and compositions thereof, respectively, are used to control a multiplicity of fungi in field crops, such as potatoes, sugar beet, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soy, rapeseed, vegetables, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables such as cucumbers, tomatoes, beans or pumpkins.
[0163] The term "plant propagation material" is to be understood as denoting all generative parts of the plant, such as seeds and plant vegetative material, such as cuttings and tubers (eg potatoes), which can be used for multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, sprouts, buds and other plant parts, including seedlings and young plants, which must be transplaned after germination or after emergence from the soil. These young plants can also be protected before transplanting by a total or partial treatment by dipping or pouring.
[0164] Preferably, the treatment of plant propagation materials with compounds I and compositions thereof, respectively, is used to control a variety of fungi in cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
[0165] The term “cultivated plants” is to be understood to include plants that have been modified by crossing, mutagenesis or genetic engineering, including but not limited to agricultural biotech products on the market or in development (cf. http://cera-gmc .org/ see GM crop database in it). Genetically modified plants are plants whose genetic material has been modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by crossing, mutation or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include, but are not limited to, targeted post-translational modification of protein(s), oligo or polypeptides, for example by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
[0166] Plants that have been modified by crossing, mutagenesis or genetic engineering, for example, have been made tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleaching herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors, such as acetyl-CoA-carboxylase (ACCase) inhibitors; or oxynyl herbicides (i.e., bromoxynil or ioxynil) as a result of conventional breeding or genetic engineering methods. In addition, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, herbicides. auxin or ACCase inhibitors. These herbicide resistance technologies are described, for example, in Pest Managem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Southern. J. Agriculture Res. 58, 2007, 708; Science 316, 2007, 1185; and references cited therein. Several cultivated plants have been made tolerant to herbicides by conventional breeding methods (mutagenesis), eg Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, eg Imazamox sunflowers or ExpressSun® (DuPont, USA ) being tolerant to sulfonyl ureas, for example tribenuron. Genetic engineering methods have been used to make crop plants such as soybeans, cotton, corn, sugar beets and rapeseed tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (Glyphosate tolerant, da Monsanto, USA), Cultivance® (tolerant to imidazolinone, BASF SE, Germany) and LibertyLink® (tolerant to glufosinate, Bayer CropScience, Germany).
[0167] In addition, plants are also covered that are by the use of recombinant DNA techniques capable of synthesizing one or more insecticidal proteins, especially those that are known from the Bacillus genus of bacteria, particularly from Bacillus thuringiensis, such as δ-endotoxins, for example, CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP), for example, VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from nematode colonizing bacteria, eg Photohabdus spp. Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnoid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lecithins, such as pea or barley lecithins; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome inactivating proteins (RIP), such as ricin, corn-RIP, abrin, luphine, saporin or briodin; steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid ID-glycosyl transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA reductase; ion channel blockers, such as sodium or calcium channel blockers; juvenile hormonal esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention, these insecticidal proteins or toxins are to be expressly understood also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains (see, for example, WO 02/015701). Other examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 and WO 03/52073. Methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the aforementioned publications. These insecticidal proteins contained in genetically modified plants give the plants, which produce these proteins, tolerance to harmful pests from all taxonomic groups of arthropods, especially for beetles (Coeloptera), double-winged insects (Diptera) and moths (Lepidoptera) and nematodes (Nematode). Genetically modified plants capable of synthesizing one or more insecticidal proteins are, for example, described in the publications mentioned above, and some of which are commercially available, such as YieldGard® (maize cultivars producing the toxin Cry1Ab), YieldGard® Plus (cultivars of corn producing the toxins Cry1Ab and Cry3Bb1), StarLink® (maize cultivars producing the toxin Cry9c), Herculex® RW (maize cultivars producing Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars that produce Cry1Ac toxin), Bollgard® I (cotton cultivars that produce Cry1Ac toxin), Bollgard® II (cotton cultivars that produce Cry1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars that produce a VIP toxin); NewLeaf® (potato cultivars that produce Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (eg Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France (maize cultivars that produce Cry1Ab toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (Maize cultivars producing a modified version of the Cry3A toxin, cf WO 03/018810), MON 863 from Monsanto Europe SA, Belgium (Maize cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe SA, Belgium (cotton cultivars that produce a modified version of the Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium (maize cultivars that produce the Cry1F toxin and the PAT enzyme).
[0168] In addition, plants are also covered by the use of recombinant DNA techniques capable of synthesizing one or more proteins in order to increase the resistance or tolerance of these plants to bacterial, viral or fungal pathogens. Examples of such proteins are so-called “pathogenesis-related proteins” (PR proteins, see eg EP-A 392 225), plant disease resistance genes (eg potato cultivars, which express acting resistance genes against Phytophthora infestans derived from Mexican wild potato Solanum bulbocastanum) or T4-lysozym (eg potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). Methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
[0169] In addition, plants are also covered by the use of recombinant DNA techniques capable of synthesizing one or more proteins to increase productivity (eg, biomass production, grain yield, starch content, oil content or content of protein), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and pathogens, fungi, bacterial or viral pathogens of these plants.
[0170] In addition, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of content substances or new content substances, specifically to improve human or animal nutrition, eg oil crops that produce acids health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (eg Nexera® rapeseed, DOW Agro Sciences, Canada).
[0171] In addition, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of content substances or new content substances, specifically to improve the production of raw material, eg potatoes that produce quantities amylopectin (eg Amflora® potato, BASF SE, Germany).
[0172] The compounds I and their compositions, respectively, are particularly suitable for controlling the following plant diseases:
[0173] Albugo spp. (white rust) on ornamentals, vegetables (eg A. candida) and sunflowers (eg A. tragopogonis); Alternaria spp. (Alternaria leaf spot) on vegetables, rapeseed (A. brassicola or brassicae), sugar beet (A. tenuis), fruits, rice, soybeans, potato (for example A. solani or A. alternata), tomatoes (for example , A. solani or A. alternata) and wheat; Aphanomyces spp. in sugar beet and vegetables; Ascochyta spp. in cereals and vegetables, for example, A. tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e.g. Leaf Rust (D. maydis) or Northern Rust (B. zeicola) on maize, e.g. spotted spot (B. sorokiniana) on cereals and by example, B. oryzae on rice and peat; Blumeria (formerly Erysiphe) graminis (powdery mildew) in cereals (eg in wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: gray mold) on fruits and berries (eg strawberries), vegetables (eg lettuce, carrots, celery and cabbage), rapeseed, flowers, vines, forest plants and wheat; Bremia lactucae (mildew) on lettuce; Ceratocystis (syn. Ophiostoma spp.) (rot or wilt) on broad-leaved and evergreen trees, eg C. ulmi (Dutch elm disease) on elm trees; Cercospora spp. (Cercospora leaf spots) on maize (eg, gray leaf spot: C. zeae-maydis), rice, sugar beet (eg, C. beticola), sugarcane, vegetables, coffee, soybeans (by example, C. sojina or C. kikuchii) and rice; Cladosporium spp. in tomatoes (eg C. fulvum: leaf mold) and cereals, eg C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) in cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on maize (C. carbonum), cereals (eg C. sativus anamorph: B. sorokiniana) and rice (eg C. miyabeanus anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) in cotton (eg C. gossypii), corn (eg C. graminicola: Anthracnose stalk rot), soft fruits, potatoes (eg C. coccodes: black dot), beans (eg , C. lindemuthianum) and soybeans (for example, C. truncatum or C. gloeosporioides); Corticium spp., for example, C. sasakii (sheath rust) on rice; Corynespora cassiicola (leaf spots) on soybean and ornamental plants; Cycloconium spp., for example C. oleaginum on olive trees; Cylindrocarpon spp. (eg, decline of tree canker or young vine, teleomorph: Nectria or Neonectria spp.) in fruit trees, vines (eg, C. liriodendri, teleomorph: Neonectria liriodendri: Black foot disease) and ornamental plants; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) in soybean; Diaporthe spp., for example, D. phaseolorum (damping) on soybeans; Drechslera (syn. Helminthosporium teleomorph: Pyrenophora) spp. in corn, cereals such as barley (eg D. teres, liquid spot) and wheat (eg D. tritici-repentis: tan spot), rice and peat; Esca (dieback, apoplexi) in vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (formerly Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. in fruits of pips (E. pyri), soft fruits (E. veneta: anthracnose) and vines (E. ampelina: anthracnose); Entyloma oryzae (coal sheet) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beet (E. betae), vegetables (eg E. pisi), such as cucurbits (eg E. cichoracearum), cabbage, rapeseed (eg E. cruciferarum); Eutypa lata (Eutypa cancer or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. in corn (eg E. turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or head rust) on cereals (eg wheat or barley), F. oxysporum on tomatoes, F. solani (f. sp., glycines now syn. F. virguliforme) and F. tucumaniae and F. brasiliense, each causing sudden death syndrome in soybean, and F. verticillioides in corn; Gaeumannomyces graminis (take-all) in cereals (eg wheat or barley) and corn; Gibberella spp. in cereals (eg G. zeae) and rice (eg G. fujikuroi: Bakanae's disease); Glomerella cingulata on vines, pome fruit and other plants and G. gossypii on cotton; Complex grain stain on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous and juniper plants, for example, G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera teleomorph: Cochliobolus) in maize, cereals and rice; Hemileia spp., for example, H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) in grapevines; Macrophomina phaseolina (sin. phaseoli) (root and stem rot) in soybean and cotton; Microdochium (syn. Fusarium) nivale (Pink snow mold) in cereals (eg wheat or barley); Microsphaera diffusa (powdery mildew) in soybean; Monilinia spp., for example M. laxa, M. fructicola and M. fructigena (white flower and branch rot, brown rot) on stone fruits and other rose plants; Mycosphaerella spp. in cereals, bananas, soft fruits and peanuts, such as for example M. graminicola (anamorph: Septoria tritici, Septoria spot) on wheat or M. fijiensis (Black Sigatoka disease) on bananas; Peronospora spp. (mildew) in cabbage (eg P. brassicae), rapeseed (eg P. parasitica), onions (eg P. destructor), tobacco (P. tabacina) and soybeans (eg P. manshurica) ; Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybean; Phialophora spp. for example, in vines (eg P. tracheiphila and P. tetraspora) and soybeans (eg P. gregata: stem rot); Phoma lingam (root and stem rot) in rapeseed and cabbage and P. betae (root rot, leaf spot and dampening) in sugar beet; Phomopsis spp. in sunflowers, vines (eg, P. viticola: tin and leaf spot) and soybeans (eg, stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (eg P. capsici), soybeans (eg P. megasperma sin. P. soybeane), potatoes and tomatoes ( eg P. infestans: late blight) and broadleaved trees (eg P. ramorum: sudden oak death); Plasmodiophora brassicae (beaten root) on cabbage, rape, radish and other plants; Plasmopara spp., eg P. viticola (vine mildew) on vines and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hops, pommel and soft fruits, eg P. leucotricha on apples; Polymyxa spp., for example, on cereals such as barley and wheat (P. graminis) and sugar beet (P. betae) and by viral diseases transmitted thereby; Pseudocercosporella herpotrichoides (eyespot, telemorph: Tapesia yallundae) on cereals, eg wheat or barley; Pseudoperonospora (mildew) on various plants, eg P. cubensis on cucurbits or P. humili on hops; Pseudopezicula tracheiphila (red fire disease or “rotbrenne”, anamorph: Phialophora) in vines; Puccinia spp. (rust) on various plants, eg P. triticina (brown or leaf rust), P. striiformis (striped or yellow rust), P. hordei (dwarf rust), P. graminis (stems or black rust) or P. recondita (brown or leaf rust) on cereals such as for example wheat, barley or rye, P. kuehnii (orange rust) on sugarcane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. teres (liquid spot) on barley; Pyricularia spp., for example, P. oryzae (teleomorph: Magnaporthe grisea, rice coup) on rice and P. grisea on peat and cereals; Pythium spp. (damping) in peat, rice, corn, wheat, cotton, rapeseed, sunflower, soybean, sugar beet, vegetables and various other plants (for example, P. ultimum or P. aphanidermatum); Ramularia spp., for example, R. collo-cygni (Ramularia leaf spots, physiological leaf spots) on barley and R. beticola on sugar beet; Rhizoctonia spp. in cotton, rice, potatoes, peat, maize, rapeseed, potatoes, sugar beet, vegetables and various other plants, eg R. solani (root and stem rot) in soybean, R. solani (rust sheath) in rice or R. cerealis (Rhizoctonia Pest) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) in rice; Sclerotinia spp. (stem rot or white mold) in vegetables and field crops such as rapeseed, sunflowers (eg S. sclerotiorum) and soybeans (eg S. rolfsii or S. sclerotiorum); Septoria spp. on various plants, for example, S. glycines (brown spot) on soybean, S. tritici (Septoria spot) on wheat and S. (syn. Stagonospora) nodorum (Stagonospora spot) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines; Setospaeria spp. (leaf rust) on maize (eg S. turcicum sin. Helminthosporium turcicum) and peat; Sphacelotheca spp. (smut) in maize, (eg S. reiliana: dirty head), sorghum and sugar cane; Sphaerotheca fuliginea (powdery mildew) in cucurbits; Spongospora subterranea (pulverulent scab) on potatoes and thus transmitted viral diseases; Stagonospora spp. in cereals, e.g. S. nodorum (Stain Stagonospora, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) in wheat; Synchytrium endobioticum in potatoes (potato wart); Taphrina spp., for example, T. deformans (curled leaf disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp. (black root rot) in tobacco, pome fruit, vegetables, soy and cotton, eg T. basicola (syn. Chalara elegans); Tilletia spp. (common or smelly) on cereals, such as for example T. tritici (syn. T. caries, wheat weevil) and T. controversa (dwarf weevil) on wheat; Typhula incarnata (grey mold) on barley or wheat; Urocystis spp., for example U. occulta (stem rust) on rye; Uromyces spp. (rust) on vegetables such as beans (e.g. U. appendiculatus sin. U. phaseoli) and sugar beet (e.g. U. betae); Ustilago spp. (loose dirt) in cereals (eg U. nuda and U. avaenae), corn (eg U. maydis: corn dirt) and sugar cane; Venturia spp. (scabies) on apples (eg V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and crops, for example, V. dahliae in strawberries, rapeseed, potatoes and tomatoes.
[0174] In a preferred embodiment, the compounds I and their compositions, respectively, are particularly suitable for controlling the following plant diseases: Puccinia spp. (rust) on various plants, for example but not limited to P. triticina (brown or leaf rust), P. striiformis (striped or yellow rust), P. hordei (dwarf rust), P. graminis (stem rust) or black) or P. recondita (brown or leaf rust) on cereals such as for example wheat, barley or rye and Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybean.
[0175] The compounds I and compositions thereof, respectively, are also suitable for the control of harmful fungi in the protection of stored products or harvesting and in the protection of materials.
[0176] The term "materials protection" should be understood as denoting the protection of technical and non-living materials, such as adhesives, glues, wood, paper and cardboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fibers or fabrics. against infestation and destruction by harmful microorganisms such as fungi and bacteria. As for the protection of wood and other materials, special attention is given to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp. .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., and in addition in protecting stored produce and harvesting the following yeast fungi are of note: Candida spp. and Saccharomyces cerevisae.
[0177] The treatment method according to the invention can also be used in the field of protection of stored products or harvest against attack by fungi and microorganisms. According to the present invention, the term "stored products" is understood to denote natural substances of plant or animal origin and their processed forms, which have been removed from the natural life cycle and for which long-term protection is desired. Stored products of plant origin, such as plants or parts thereof, for example, stems, leaves, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, crushed, ground, pressed or roasted, a process that is also known as post-harvest treatment. It also falls within the definition of timber stored products (timber), whether in the form of raw wood, such as construction timber, electricity poles and barriers, or in the form of finished articles, such as furniture or objects made from wood. Stored products of animal origin are rawhide, leather, skins, hair and the like. The combinations according to the present invention can avoid disadvantageous effects such as decay, discoloration or mold. Preferably, "stored products" means natural substances of vegetable origin and their processed forms, more preferably fruits and their processed forms, such as pomoids, stone fruits, soft and citrus fruits and their processed forms .
[0178] The compounds of formula I may be present in different crystal modifications whose biological activity may differ. They are also the subject matter of the present invention.
[0179] Compounds I are used as such or in the form of compositions treating fungi or plants, plant propagation materials such as seeds, soil, surfaces, materials or divisions to be protected from fungal attack with a fungicidally effective amount of active substances. Application can be carried out either before or after infection of plants, plant propagation materials such as seeds, soil, surfaces, materials or areas by the fungi.
[0180] Plant propagation materials can be treated with compounds I as such or with a composition comprising at least one compound I prophylactically on or before planting or transplanting.
[0181] The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.
[0182] An agrochemical composition comprises a fungicidally effective amount of a compound I. The term "effective amount" denotes an amount of the composition or compounds I that is sufficient to control harmful fungi in cultivated plants or in the protection of materials and which does not results in substantial damage to the treated plants. Such amount can vary over a wide range and depends on several factors, such as the fungal species to be controlled, the plant or cultivated material treated, the climatic conditions and the specific compound I used.
[0183] The compounds I, the N-oxides and salts thereof can be converted into usual types of agrochemical compositions, for example, solutions, emulsions, suspensions, dusts, powders, pastes, granules, presses, capsules and mixtures thereof. Examples of composition types are suspensions (eg SC, OD, FS), emulsifiable concentrates (eg EC), emulsions (eg EW, EO, ES, ME), capsules (eg CS, ZC) , pastes, pellets, wettable powders or dusts (eg WP, SP, WS, DP, DS), presses (eg BR, TB, DT), granules (eg WG, SG, GR, FG, GG , MG), insecticidal articles (eg LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (eg GF). These and other types of compositions are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph no. 2, 6th Ed. May 2008, CropLife International.
[0184] The compositions are prepared in a known manner, as described by Mollet and Grubemann, Formulation Technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T & F Informa, London, 2005.
[0185] Suitable auxiliaries are solvents, liquid vehicles, solid vehicles or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellants, attractants, food stimulants , compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, dyes, tackifiers and binders.
[0186] Suitable liquid solvents and vehicles are water and organic solvents such as medium to high boiling mineral oil fractions, eg kerosene, diesel oil; vegetable or animal oils; aliphatic, cyclic and aromatic hydrocarbons, for example toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, for example ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, for example cyclohexanone; esters, for example lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, for example N-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.
[0187] Suitable solid carriers or fillers are mineral earths, for example, silicates, silica gel, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, oxide magnesium; polysaccharides, for example, cellulose, starch; fertilizers, eg ammonium sulphate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, eg cereal flour, tree bark flour, wood flour, nutshell flour and mixtures thereof.
[0188] Suitable surfactants are surface active compounds such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes and mixtures thereof. Such surfactants can be used as an emulsifier, dispersant, solubilizer, wetting agent, penetration enhancer, protective colloid or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
[0189] Suitable anionic surfactants are alkaline, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, fatty acid and oil sulfonates, ethoxylated alkylphenol sulfonates, alkoxylated arylphenol sulfonates, condensed naphthalene sulfonates, dodecyl sulfonates tridecylbenzenes, naphthalene sulfonates and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and ethoxylated carboxylated alcohol or alkylphenols.
[0190] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar based surfactants, polymeric surfactants and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated to 1 to 50 equivalents. Ethylene oxide and/or propylene oxide can be used for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglycosides. Examples of polymeric surfactants are vinyl pyrrolidone homo- or copolymers, vinyl alcohols or vinyl acetate.
[0191] Suitable cationic surfactants are quaternary surfactants, eg quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines.
[0192] Suitable adjuvants are compounds that have negligible or no pesticidal activity, and that improve the biological performance of compound I on the target. Examples are surfactants, mineral or vegetable oils and other auxiliaries. Other examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T & F Informa UK, 2006, chapter 5.
[0193] Suitable thickeners are polysaccharides (eg xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
[0194] Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones.
[0195] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.
[0196] Suitable defoaming agents are silicones, long-chain alcohols and fatty acid salts.
[0197] Suitable dyes (eg in red, blue or green) are low water solubility pigments and water soluble dyes. Examples are inorganic dyes (eg iron oxide, titanium oxide, iron hexacyanoferrate) and organic dyes (eg alizarin-, azo- and phthalocyanine dyes).
[0198] Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes and cellulose ethers.
[0199] Examples for types of composition and their preparation are: i) Water-soluble concentrates (SL, LS) 10 to 60% by weight of a compound I and 5 to 15% by weight of wetting agent (for example, alkoxylates of alcohol) are dissolved in water and/or in a water-soluble solvent (eg alcohols) to 100% by weight. The active substance dissolves after dilution with water.ii) Dispersible Concentrates (DC) 5 to 25% by weight of a compound I and 1 to 10% by weight of dispersant (eg polyvinylpyrrolidone) are dissolved in organic solvent (by example, cyclohexanone) up to 100% by weight. Dilution with water provides a dispersion.ii i) Emulsifiable concentrates (EC) 15 to 70% by weight of a compound I and 5 to 10% by weight of emulsifiers (eg calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water insoluble organic solvent (eg aromatic hydrocarbon) up to 100% by weight. Dilution with water provides an emulsion.iv) Emulsions (EW, EO, ES) 5 to 40% by weight of a compound I and 1 to 10% by weight of emulsifiers (eg calcium dodecylbenzenesulfonate and castor oil ethoxylate ) are dissolved in 20 to 40% by weight of water-insoluble organic solvent (eg aromatic hydrocarbon). This mixture is introduced in water up to 100% by weight by means of an emulsifying machine and transformed into a homogeneous emulsion. Dilution with water provides an emulsion.v) Suspensions (SC, OD, FS) In an agitated ball mill, 20 to 60% by weight of a compound I is ground with the addition of 2 to 10% by weight of dispersants and wetting agents (eg sodium lignosulphonate and alcohol ethoxylate), 0.1 to 2% by weight thickener (eg xanthan gum) and water up to 100% by weight to give a fine suspension of the active substance. Dilution with water provides a stable suspension of the active substance. For composition of type FS, up to 40% by weight of binder (eg polyvinyl alcohol) is added.vi) Water-dispersible granules and water-soluble granules (WG, SG) 50 to 80% by weight of a compound I is finely ground with addition of dispersants and wetting agents (eg sodium lignosulphonate and ethoxylated alcohol) to 100% by weight and prepared in the form of water-dispersible or water-soluble granules by means of technical apparatus (eg extrusion, tower spray, fluidized bed). Dilution with water provides a stable dispersion or solution of the active substance.vii) Water-dispersible powders and water-soluble powders (WP, SP, WS) 50 to 80% by weight of a compound I is ground in a rotor-mill. stator with addition of 1 to 5% by weight of dispersants (eg sodium lignosulfonate), 1 to 3% by weight of wetting agents (eg ethoxylated alcohol) and solid carrier (eg silica gel) up to 100% by weight. Dilution with water provides a stable dispersion or solution of the active substance.vii i) Gel (GW, GF) In an agitated ball mill, 5 to 25% by weight of a compound I is ground with the addition of 3 to 10% by weight of dispersants (eg sodium lignosulfonate), 1 to 5% by weight of thickener (eg carboxymethyl cellulose) and water up to 100% by weight to provide a fine suspension of the active substance. Dilution with water provides a stable suspension of the active substance.ix) Microemulsion (ME) 5 to 20% by weight of a compound I are added to a mixture of 5 to 30% by weight of organic solvent (eg acid dimethyl amide fatty acid and cyclohexanone), 10 to 25% by weight of surfactant mixture (eg ethoxylated alcohol and arylphenol ethoxylate) and water to 100%. This mixture is stirred for 1 h to spontaneously produce a thermodynamically stable microemulsion.x) Microcapsules (CS) An oil phase comprising 5 to 50% by weight of a compound I, 0 to 40% by weight of water-insoluble organic solvent ( eg aromatic hydrocarbon), 2 to 15% by weight of acrylic monomers (eg methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed in an aqueous solution of a protective colloid (eg polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5 to 50% by weight of a compound I according to the invention, 0 to 40% by weight of water-insoluble organic solvent (eg aromatic hydrocarbon) and an isocyanate monomer (eg. diphenylmethene-4,4'-diisocyanate) are dispersed in an aqueous solution of a protective colloid (eg polyvinyl alcohol). The addition of a polyamine (eg hexamethylenediamine) results in the formation of polyurea microcapsules. The monomide content at 1 to 10% by weight. The % by weight refers to the total composition of the composition CS.xi) Dustable Powders (DP, DS)1 to 10% by weight of a compound I are finely ground and mixed intimately with a solid carrier (e.g. finely divided kaolin ) up to 100% by weight.xii) Granules (GR, FG) 0.5 to 30% by weight of a compound I is finely ground and combined with the solid carrier (eg silicate) up to 100% by weight. Granulation is achieved by extrusion, spray drying or fluidized bed.xii i) Ultra-low volume (UL)1 liquids at 50% by weight of a compound I are dissolved in organic solvent (eg aromatic hydrocarbon) up to 100% in Weight.
[0200] Compositions of types i) to xiii) may optionally comprise other auxiliaries, such as 0.1 to 1% by weight of bactericides, 5 to 15% by weight of anti-freezing agents, 0.1 to 1% by weight weight of anti-foam agents, and 0.1 to 1% by weight of colorants.
[0201] Agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60% by weight of the active substance. The active substances are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
[0202] For the purpose of treating plant propagation materials, particularly seeds, seed treatment solutions (LS), Suspoemulsions (SE), fluid concentrates (FS), dry treatment powders (DS), water dispersible powders for sludge treatment (WS) water soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually used. The compositions in question provide, after a two to ten-fold dilution, active substance concentrations of between 0.01 and 60% by weight, preferably between 0.1 and 40%, in ready-to-use preparations. The application can be carried out before or during sowing. Methods for applying compound I and its compositions, respectively, to plant propagation material, especially seeds, include methods of coating, coating, pelletizing, dusting and dipping, as well as furrow application methods. Preferably, the compound I or its compositions, respectively, are applied to the plant propagation material by a method such that germination is not induced, for example, by seed coating, pelletizing, covering and dusting.
[0203] When used in phytosanitary protection, the amounts of active substances applied are depending on the type of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.
[0204] In the treatment of plant propagation materials, such as seeds, for example, by spraying, coating or dipping seeds, amounts of active substance from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and more preferably 5 to 100 g per 100 kg of plant propagation material (preferably seeds) are generally required.
[0205] When used in the protection of stored materials or products, the amount of active substance applied depends on the type of application area and the desired effect. The quantities usually applied in the protection of materials are from 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
[0206] Various types of oils, wetting agents, adjuvants, fertilizers, or micronutrients and other pesticides (eg herbicides, insecticides, fungicides, growth regulators, phytotoxicity protectants, biopesticides) can be added to the active substances, or the compositions of the comprising as a premix or if appropriate not until just before use (tank mix). These agents can be mixed together with the compositions according to the invention in a weight ratio of 1 : 100 to 100 : 1, preferably 1 : 10 to 10 : 1.
[0207] A pesticide is generally a chemical or biological agent (such as pesticide active ingredient, compound, composition, virus, bacteria, antimicrobial or disinfectant) that, through its effect, prevents, incapacitates, kills or discourages pests. Target pests can include insects, plant pathogens, weeds, molluscs, birds, mammals, fish, nematodes (round worms) and microbes that destroy property, cause nuisance, spread disease or are vectors of disease. The term “pesticide” also includes plant growth regulators that alter the expected growth, flowering or reproduction rate of plants; defoliants that cause leaves or other leaves to fall off a plant, often to facilitate harvesting; desiccants that promote drying of living tissue, such as unwanted plant tops; plant activators that activate plant physiology to defend against certain pests; phytotoxicity protectors that reduce the unwanted herbicidal action of pesticides on cultivated plants; and plant growth promoters that affect plant physiology, for example, to increase plant growth, biomass, yield or any other quality parameter of the harvestable products of a crop plant.
[0208] The user applies the composition according to the invention normally from a pre-dosing device, a back spray, a spray tank, a spray plane or an irrigation system. Usually, the agrochemical composition prepared with water, buffer and/or other auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor is applied per hectare of agricultural usable area.
[0209] According to an embodiment, the individual components of the composition according to the invention, such as parts of a kit or parts of a binary or ternary mixture, can be mixed by the user himself in a spray tank or any other type of container used for applications (eg seed treatment drums, seed pelleting machines, back sprayer) and other auxiliaries can be added if appropriate.
[0210] Accordingly, in one embodiment, the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary component and optionally an additional active component 3) as defined herein.
[0211] The mixture of compounds I or compositions comprising them in the form of use as fungicides with other fungicides results in many cases in an expansion of the spectrum of fungicidal activity to be obtained or in a prevention of a development of resistance to fungicides. Furthermore, in many cases synergistic effects are obtained.
[0212] The following list of pesticides II (eg active substances pesticides and biopesticides), together with which compounds I can be used, is intended to illustrate the possible combinations, but does not limit them: A) Respiration Inhibitors: Inhibitors of complex III at Qo site: azoxystrobin (A.1.1), coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), phenaminstrobin (A.1.6), phenoxystrobin/ fluphenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1.11), orysastrobin (A.1.12), picoxystrobin (A.1.13) , pyraclostrobin (A.1.14), pyramethostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17) 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl) -phenyl)-2-methoxyimino-N-methyl-acetamide (A.1.18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb (A.1.20), famoxadone (A.1.21), fenamidone (A.1.21) methyl- N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)ox ylmethyl]phenyl]-N-methoxy-carbamate (A.1.22), 1-[3-chloro-2-[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl]phenyl]-4- methyl-tetrazol-5-one (A.1.23), 1-[3-bromo-2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5- one (A.1.24), 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (A.1.25 ), 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one (A.1.26), 1-[ 2-[[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one (A.1.27), 1-[2-[ [4-(4-chlorophenyl)thiazol-2-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (A.1.28), 1-[3-chloro-2-[[ 4-(p-tolyl)thiazol-2-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one (A.1.29), 1-[3-cyclopropyl-2-[[2-methyl-4- (1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one (A.1.30), 1-[3-(difluoromethoxy)-2-[[2-methyl-4- (1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one (A.1.31), 1-methyl-4-[3-methyl-2-[[2-methyl- 4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]tetrazole -5-one (A.1.32), 1-methyl-4-[3-methyl-2-[[1-[3-(trifluoromethyl)phenyl]-ethylideneamino]oxymethyl]phenyl]tetrazol-5-one (A. 1.33), (Z, 2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N, 3-dimethyl-pent-3-enamide (A.1.34), (Z, 2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.35), pyriminostrobin (A.1.36 ), bifujunzhi (A.1.37), 2-(ortho-((2,5-dimethylphenyl-oxymethylene)phenyl-3-methoxy-acrylic acid methylester (A.1.38).- Inhibitors of complex III at the Qi site: cyazofamide (A.2.1),amisulbrom (A.2.2), [(6S, 7R, 8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl -4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate (A.2.3), [2-[[(7R, 8R, 9S)-7-benzyl-9-methyl-8-( 2-methylpropanoyloxy)-2,6-dioxo-1,5-dioxonan-3-yl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl-2-methylpropanoate (A.2.4), [(6S, 7R, 8R )-8-benzyl-3-[[4-methoxy-3-(propanoyloxy-methoxy)pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2- methylpropanoate (A.2.5).- Inhibitor complex II es: benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalide (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A. .3.7), flutolanil (A.3.8), fluxapyroxade (A.3.9), furametpyr (A.3.10), isofetamide (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.11) 3.14), penflufen (A.3.1 5), penthiopyrad (A.3.1 6), 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2, 4, 6-trichlorophenyl) )ethyl]pyrazole-4-carboxamide (A.3.17), N-[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide (A.3.18)sedaxane (A.3.19) , teclophthalam (A.3.20), thifluzamide (A.3.21), 3-(difluoromethyl)-1-methyl-N-(1, 1, 3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.22) , 3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide(A.3.23),1,3-dimethyl-N-(1,1, 3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.24), 3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazol-4-yl carboxamide (A.3.25), 1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyraz ol-4-carboxamide (A.3.26), 3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.27), 3 -(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide (A.3.28), methyl (E)-2-[ 2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), N-[(5-chloro-2-isopropyl-phenyl)methyl] -N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide(A.3.31), 2-(difluoromethyl)-N-(1,1,3-trimethyl-indan-4- il) pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2 -(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3- ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl) pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]-pyridine-3-carboxamide (A.3.37 ), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-i ndan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indan-4-yl]pyridine-3- carboxamide (A.3.39).- Other respiration inhibitors: diflumethorim (A.4.1); nitrophenyl derivatives: binapacril (A.4. 2) dinobuton (A.4.3) dinocap (A.4.4) fluazinam (A.4.5) meptildinocap (A.4.6) ferimzone (A.4.7); organometallic compounds: fentin salts, eg fentin acetate (A.4.8) fentin chloride (A.4.9) or fentin hydroxide (A.4.10); amethoctradine (A.4.11); siltiofam (A.4.12).B) Inhibitors of sterol biosynthesis (SBI fungicides)- C14 demethylase inhibitors: triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole (B.B. .1.4), difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazol ( B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B .1.19), paclobutrazol (B.1.20), penconazol (B.1.21), propiconazol (B.1.22), prothioconazol (B.1.23), simeconazol (B.1.24), tebuconazol (B.1.25), tetraconazol (B.1.25). 1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazol (B.1.29), uniconazol (B.1.30), 1-[rel- (2S; 3R)-3-(2-chlorophenyl)- 2-(2, 4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1H-[1,2,4]triazole (B.1.31), 2-[rel-(2S; 3R)-3-(2-chlorophenyl) )-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1,2,4]triazol-3-thiol (B.1.32), 2-[2-chloro-4-(4-cl orophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol (B.1.33), 1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]- 1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol (B.1.34) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1, 2 , 4-triazol-1-yl)butan-2-ol (B.1.35), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1- yl)butan-2-ol (B.1.36), 2-[4-(4-chloro-phenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1 -yl)butan-2-ol (B.1.37), 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan- 2-ol (B.1.38), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol (B.1.39), 2[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol (B.1.40), 2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)]phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (B.1.41), 2-[2 -chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent-3-yn-2-ol (B.1. 42), 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1.4 4), pefurazoate (B.1.4 5), prochloraz (B.1.4 6), triflumizole (B.1.47); pyrimidines, pyridines and piperazines: fenarimol (B.1.49), pyrifenox (B.1.50), triforine (B.1.51), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-di) fluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52).- Delta-14-reductase inhibitors: aldimorphs (B.2.1), dodemoryl (B.2.2), dodemoropho-acetate (B. 2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8).- 3-keto reductase inhibitors: fenhexamide (B. 3.1).- Other sterol biosynthesis inhibitors: chlorphenomizol (B.4.1). C) Nucleic acid synthesis inhibitors- Phenylamylamides or amino acid fungicides from acyl:benalaxyl (C.1.1), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7).- Other inhibitors of nucleic acid synthesis: himexazol (C.2.1), octilinone (C.2.2), oxolinic acid (C.2.3) , bupyrimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy) pyrimidin-4-amine (C.2.7), 5-fluoro-2-(4-chlorophenylmethoxy)pyrimidine-4 amine (C.2.8).D) Cell division and cytoskeleton inhibitors Tubulin inhibitors: benomyl (D.1.1) , carbendazim (D.1.2), fuberidazole (D.1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5 -phenyl-pyridazine (D.1.6), 3-chloro-6-methyl-5-phenyl-4-(2, 4, 6-trifluorophenyl)pyridazine (D.1.7), N-ethyl-2-[( 3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methyls ulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl- 8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxy-acetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N -propyl-butanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide (D.1.13), 2-[(3- ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-( 2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl- pyrazol-3-amine (D.1.16).- Other cell division inhibitors: dietofencarb (D.2.1), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D. 2.5), metrafenone (D.2.6), pyriophenone (D.2.7).E) Inhibitors of amino acid and protein synthesis- Inhibitors of methionine synthesis: cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E .1.3). - Inhibitors of protein synthesis: blasticidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydrochloride hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracycline ( E.2.6).F) Inhibitors of signal transduction - MAP/histidine kinase inhibitors: fluoroimide (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozoline (F.1.4), fludioxonil ( F.1.5).- Protein G inhibitors: quinoxyfen (F.2.1).G) Inhibitors of lipid synthesis and membranes- Phospholipid biosynthesis inhibitors: edifenphos (G.1.1), iprobenfos (G.1.2), pyrazolophos ( G.1.3), isoprothiolane (G.1.4).- Lipid peroxidation: dichloran (G.2.1), quintazene (G.2.2), tecnazene (G.2.3), tolclophos-methyl (G.2.4), biphenyl (G .2.5), chloroneb (G.2.6), etridiazol (G.2.7) - Phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamide (G.3.3), pyrimorph ( G.3.4), bentiavalcarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7).- Compounds that affect the permeab Cell membrane ility and fatty acids: propamocarb (G.4.1).- Oxysterol binding protein inhibitors: oxathiapiprolin(G.5.1), 2-{3-[2-(1-{[3, 5-bis(difluoromethyl) -1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonate (G. 5.2), 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)1, 3-thiazol-4-yl ]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate (G.5.3) 4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.4), 4-[1-[2-[3, 5-bis(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl) pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl) )pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridin-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-( trifluoromethyl)pyrazol-1-yl]acetyl]-4-pi peridyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl] -4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[3, 5-bis(trifluoromethyl)pyrazol-1-yl]acetyl] - 4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl] acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (L.5.11).H) Inhibitors with Multi-Local Action- Inorganic active substances: Bordeaux mixture (H.1.1), copper (H) .1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7).- Thio - and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), tiram (H. 2.7), zineb (H.2.8), ziram (H.2.9).- Organochlorine compounds: anilazine (H.3.1), chlorothalonil (H.3.2),captafol (H.3.3),captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophene (H. 3, 7), hexachlorobenzene (H.3.8), pentachlorphenol (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.11).- Guanidines and others: guanidine (H.4.1), dodine ( H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine acetate (H.4.5), iminoctadine (H.4.6) iminoctadine-triacetate (H.4.7), iminoctadine-tris (albesylate ) (H.4.8), dithianone (H.4.9), 2,6-dimethyl-1H, 5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3, 5, 7(2H, 6H)-tetraone (H.4.10).I) cell wall synthesis inhibitors- Glucan synthesis inhibitors: validamycin (I.1.1), polyoxin B (I.1.2).- Synthesis inhibitors of melanin: pyroquilone (I.2.1), tricyclazole (I.2.2), carpropamide (I.2.3), dicyclomet (I.2.4), fenoxanil (I.2.5). J) Plant defense inducers- Acibenzolar-S-methyl (J.1.1), probenazol (J.1.2), isotianil (J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl-aluminium (J.1.7), phosphorous acid and its salts (J.1.8), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-N-(2, 4 -dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10).K) Mode of action unknown - Bronopol (K.1.1), chinomethionate (K.1.2), ciflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclocimet (K.1.7), diclomezine (K.1.8), difenzoquat (K.1.9), difenzoquat-methylsulfate (K.1.10), diphenylaamin (K.1.11), fenitropan (K.1.12), fenpyrazamine (K.1.13), flumethover (K.1.14), flusulfamide (K.1.15), flutianil (K.1.16), harpin (K.1.17), methasulfocarb (K.1.18), nitrapirin (K.1.19), nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21), oxyn-copper (K.1.22), proquinazid (K.1.23), tebufloquin (K.1.24), teclophthalam (K.1.25) ), triazoxide (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-formamidine methyl (K.1.27), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methylformamidine (K.1.2 8), N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl- N-methyl-formamidine (K.1.29), N'-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (K.1.30) , N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.31), N' -[5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N'-[5-bromo-2-methyl- 6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)- phenyl)-N-ethyl-N-methyl-formamidine (K.1.34), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine (K.1.35), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide (K 1.36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (pyrisoxazol) (K.1.37), 3-[5-(4-methylphenyl) -2,3-dimethyl-isoxazolidin-3-yl]-pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl 1-1H-benzoimidazole (K.1.39), (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40), picarbutrazox (K.1.41), N-[ Pentyl 6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.42), but-3-ynyl-N-[ 6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]-amino]oxymethyl]-2-pyridyl]carbamate (K.1.43), 2-[2-[(7,8) -difluoro-2-methyl-3-quinolyl)oxy]-6-fluorophenyl]propan-2-ol (K.1.44), 2-[2-fluoro-6-[(8-fluoro-2-methyl-3- quinolyl)oxy]phenyl]propan-2-ol (K.1.45), 3-(5-fluoro-3,3,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline (K. 1.46), quinoline (K.1.47), 3-(4,4,5-trifluoro-3, 3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline (K.1.48), 9-fluoro-2, 2-dimethyl-5-(3-quinolyl)-3H-1,4-benzoxazepine (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3 - fluoro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), 3-[(3,4-dichloroisothiazol-5-yl)methoxy]1,2 1,1-dioxide -benzothiazole (K.1.52), N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl -formamidine (K.1.53).M) Growth regulators- abscisic acid (M.1.1), amidochlor, ancimidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dimethipine, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione, prohexadione-calcium, prohydrojasmon, thidiazuron, triapentenol, tributyl phosphorotrithioate, 2,3,5-tri-iodobenzoic acid, trinexapac-ethyl and uniconazol; N) Herbicides of classes N.1 to N.15-N .1 Lipid biosynthesis inhibitors: aloxidim (N.1.1), aloxidim-sodium (N.1.2), butroxydim (N.1.3), cletodim (N.1.4), clodinafop (N.1.5), clodinafop-propargyl (N. .1.6), cyclooxydim (N.1.7), cialofop (N.1.8), cialofop-butyl (N.1.9), diclofop (N.1.10), diclofop-methyl (N.1.11), fenox aprop (N.1.12), fenoxaprop-ethyl (N.1.13), fenoxaprop-P (N.1.14), fenoxaprop-P-ethyl (N.1.15), fluazifop (N.1.16), fluazifop-butyl (N.1.17 ), fluazifop-P (N.1.18), fluazifop-P-butyl (N.1.19), haloxyfop (N.1.20), haloxyfop-methyl (N.1.21), haloxyfop-P (N.1.22), haloxyfop-P -methyl (No.1.23), metamifop (No.1.24), pinoxaden (No.1.25), profoxydim (No.1.26), propaquizafop (No.1.27), quizalofop (No.1.28), quizalofop-ethyl (No.1.29 ), quizalofop-tefuryl (N.1.30), quizalofop-P (N.1.31), quizalofop-P-ethyl (N.1.32), quizalofop-P-tefuryl (N.1.33), sethoxydim (N.1.34), tepraloxydim (N.1.35), tralkoxydim (N.1.36), 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2 ,2,6,6-tetramethyl-2H-pyran-3(6H)-one ((N.1.37), CAS 1312337-72-6); 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H) -one ((N.1.38), CAS 1312337-45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3( 6H)-one ((N.1.39), CAS 103375793-5); 4-(2'4'-Dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)- dione ((N.1.40), CAS 1312340-84-3); 5-(α-cetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2, 2, 6, 6 -tetramethyl-2H-pyran-3-one ((N.1.41), CAS 1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl -2H-pyran-3-one (N.1.42); 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2, 2, 6, 6- tetramethyl-2H-pyran-3-one ((N.1.43), CAS 1312340-82-1); 5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl- 2H-pyran-3-one ((N.1.44), CAS 1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo- 2H-pyran-3-yl methyl carboxylic acid ester ((N.1.45), CAS 1312337-51-1); 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H -pyran-3-yl methyl ester of carbonic acid (N.1.46); 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo- 2H-pyran-3-yl methyl ester of carbonic acid ((N.1.47), CAS 1312340-83-2); 4-(2',4'-dichloro-4-ethyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H -pyran-3-yl methyl ester of carbonic acid ((N.1.48), CAS 1033760-58-5); benfuresate (N.1.49), butylate (N.1.50), cycloate (N.1.51), dalapon (N.1.52), dimepiperate (N.1.53), EPTC (N.1.54), esprocarb (N.1.55), ethofumesate (N.1.56), flupropanate (N.1.57), molinate (N.1.58), orbencarb (N.1.59), pebulate (N.1.60), prosulfocarb (N.1.61), TCA (N.1.62), thiobencarb ( N.1.63), thiocarbazil (N.1.64), triallate (N.1.65), and vernolate (N.1,66);- N.2 ALS inhibitors: amidosulfuron (N.2.1), azimsulfuron (N.2.2) ,bensulfuron (N.2.3),bensulfuron-methyl (N.2.4), chlorimuron (N.2.5), chlorimuron-ethyl (N.2.6), chlorsulfuron (N.2.7), cinosulfuron (N.2.8), cyclosulfamuron (N .2.9), ethametsulfuron (N.2.10), ethametsulfuron-methyl (N.2.11), ethoxysulfuron (N.2.12), flazasulfuron (N.2.13), fluketosulfuron (N.2.14), flupyrsulfuron (N.2.15), flupyrsulfuron- methyl-sodium (N.2.16), foramsulfuron (N.2.17), halosulfuron (N.2.18), halosulfuron-methyl (N.2.19), imazosulfuron (N.2.20), iodosulfuron (N.2.21), iodosulfuron-methyl- sodium (N.2.22), iofensulfuron (N.2.23), iofensulfuron-sodium (N.2.24) , mesosulfuron (N.2.25), metazosulfuron (N.2.26), metsulfuron (N.2.27), metsulfuron-methyl (N.2.28), nicosulfuron (N.2.29), orthosulfamuron (N.2.30), oxasulfuron (N.2.31 ), primisulfuron (N.2.32), primisulfuron-methyl (N.2.33), propirisulfuron (N.2.34), prosulfuron (N.2.35), pyrazosulfuron (N.2.36), pyrazosulfuron-ethyl (N.2.37), rimsulfuron (N.2.37) N.2.38), sulfometuron (N.2.39), sulfometuron-methyl (N.2.40), sulfosulfuron (N.2.41), thifensulfuron (N.2.42), thifensulfuron-methyl (N.2.43), triasulfuron (N.2.44) ,tribenuron (N.2.45), tribenuron-methyl (N.2.46), trifloxysulfuron (N.2.47), triflusulfuron (N.2.48), triflusulfuron-methyl (N.2.49), tritosulfuron (N.2.50), imazametabenz (N.2.50) .2.51), imazametabenz-methyl (N.2.52), imazamox (N.2.53), imazapic (N.2.54), imazapyr (N.2.55), imazaquin (N.2.56), imazethapyr (N.2.57); chloransulam (N.2.58), chloransulam-methyl (N.2.59), diclosulam (N.2.60), flumetsulam (N.2.61), florasulam (N.2.62), metosulam (N.2.63), penoxsulam (N.2.64) , pyrimisulfan (N.2.65), and pyroxsulam (N.2.66); bispyribac (N.2.67), bispyribac-sodium (N.2.68), pyribenzoxim (N.2.69), piriftalid (N.2.70), pyriminobac (N.2.71), pyriminobac-methyl (N.2.72), pyrithiobac (N.2.70). 2.73), pyrithiobac-sodium (N.2.74), 4-[[[2-[(4, 6-dimethoxy-2-pyrimidinyl), oxy]phenyl]methyl]amino]benzoic acid-1-methyl-ethyl ester ( (N.2.75), CAS 420138-41-6), 4-[[[2-[(4, 6-dimethoxy-2-pyrimidinyl), oxy]phenyl]methyl]amino]-benzoic acid propyl ester (( N.2.76), CAS 420138-40-5), N-(4-bromophenyl)-2-[(4, 6-dimethoxy-2-pyrimidinyl), oxy]benzenemethanamine ((N.2.77), CAS 420138-01 -8); flucarbazone (N.2.78), flucarbazone-sodium (N.2.79), propoxycarbazone (N.2.80), propoxycarbazone-sodium (N.2.81), tiencarbazone (N.2.82), tiencarbazone-methyl (N.2.83), triafamone (N.2.83) N.2.84);- N.3 photosynthesis inhibitors: amicarbazone (N.3.1); chlorotriazine (N.3.2); amethrin (N.3.3), atrazine (N.3.4), chloridazone (N.3.5), cyanazine (N.3.6), desmethrin (N.3.7), dimethathrin (N.3.8), hexazinone (N.3.9), metribuzin (N.3.10), prometon (N.3.11), promethrin (N.3.12), propazine (N.3.13), simazine (N.3.14), simetrin (N.3.15), terbumeton (N.3.16), terbuthylazin ( N.3.17), terbutryn (N.3.18), triethazine (N.3.19); chlorobromuron (N.3.20), chlortoluron (N.3.21), chloroxuron (N.3.22), dimefuron (N.3.23), diuron (N.3.24), fluometuron (N.3.25), isoproturon (N.3.26), isouron (N.3.27), linuron (N.3.28), metamitron (N.3.29), metabenzthiazuron (N.3.30), methobenzuron (N.3.31), metoxuron (N.3.32), monolinuron (N.3.33), neburon ( N.3.34), siduron (N.3.35), tebuthiron (N.3.36), thiadiazuron (N.3.37), desmedipham (N.3.38), karbutilat (N.3.39), phenmedipham (N.3.40), phenmedipham-ethyl (N.3.41), bromophenoxim (N.3.42), bromoxynil (N.3.43), and its salts and esters, ioxynil (N.3.44), and its salts and esters, bromacyl (N.3.45), lenacil (N. 3, 46), terbacil (N.3.47), bentazon (N.3.48), bentazon-sodium (N.3.49), pyridate (N.3.50), pyridafol (N.3.51), pentanochlor (N.3.52), propanyl (No.3, 53); diquat (N.3.54), diquat dibromide (N.3.55), paraquat (N.3.56), paraquat dichloride (N.3.57), paraquat dimethylsulfate (N.3.58);- N.4 protoporphyrinogen oxidase inhibitors IX: acifluorfen (N.4.1), acifluorfen-sodium (N.4.2), azafenidin (N.4.3), bencarbazone (N.4.4), benzfendizone (N.4.5), bifenox (N.4.6), butafenacyl (N. 4.7), carfentrazone (N.4.8), carfentrazone-ethyl (N.4.9), chloromethoxyphen (N.4.10), cinidon-ethyl (N.4.11), fluazolate (N.4.12), flufenpyr (N.4.13), flufenpyr -ethyl (N.4.14), flumiclorac (N.4.15), flumiclorac-pentyl (N.4.16), flumioxazine (N.4.17), fluoroglucofen (N.4.18), fluoroglycofen-ethyl (N.4.19), flutiacet (N. .4.20), fluthiacet-methyl (N.4.21), fomesafen (N.4.22), halosafen (N.4.23), lactofen (N.4.24), oxadiargyl (N.4.25), oxadiazone (N.4.26), oxyfluorfen ( N.4.27), pentoxazone (N.4.28), profluazol (N.4.29), pyraclonil (N.4.30), pyraflufen (N.4.31), pyraflufen-ethyl (N.4.32), saflufenacil (N.4.33), sulfentrazone (N.4.34), thidiazimin (N.4.35), thiafenacil (N.4 36), trifludimoxazin (N.4.37), [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1, 2,3,4-tetrahydropyrimidin- ethyl 3-yl), phenoxy]-2-pyridyloxy]acetate((N.4.38), CAS 353292-31-6), N-ethyl-3-(2,6-dichloro-4-trifluoro-methylphenoxy)- 5-methyl-1H-pyrazole-1-carboxamide ((N.4.39), CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H- 1-pyrazole-1-carboxamide ((N.4.40), CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethyl-phenoxy)-5-methyl-1H- pyrazol-1-carboxamide ((N.4.41), CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazol-1- carboxamide ((N.4.42), CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl))-3,4-dihydro-2H-benzo[1, 4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1, 3,5]triazinan-2,4-dione ((N.4.43), CAS 451484-50-7), 2- (2, 2, 7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4, 5, 6, 7- tetrahydro-isoindole-1,3-dione ((N.4.44), CAS 1300118-96-0), 1-methyl-6-trifluoro methyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H- pyrimidine-2,4-dione ((N.4.45), CAS 1304113-05-0), methyl (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl -pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate ((N.4.46), CAS 948893-00-3), 3-[7-chloro-5-fluoro- 2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione ((N.4.47), CAS 212754-02-4); - N.5 Bleaching herbicides: beflubutamid (N.5.1), diflufenican (N.5.2), fluridone (N.5.3), flurochloridone (N.5.4), flurtamone (N.5.5), norflurazone (N.5.6), picolinafen (N.5.7), 4-(3-trifluoromethyl-phenoxy)-2-(4-trifluoromethylphenyl)-pyrimidine ((N.5.8), CAS 180608-33-7); benzobicyclon (N.5.9), benzofenap (N.5.10), bicyclopyrone (N.5.11), clomazone (N.5.12), phenquintrione (N.5.13), isoxaflutole (N.5.14), mesotrione (N.5.15), pyrasulfotol (N.5.16), pyrazolinate (N.5.17), pyrazoxifene (N.5.18), sulcotrione (N.5.19), tefuryltrione (N.5.20), tembotrione (N.5.21), tolpyrate (N.5.22), topramezone ( N.5.23); aclonifen (N.5.24), amitrole (N.5.25), flumeturon (N.5.26);- N.6 EPSP synthase inhibitors: glyphosate (N.6.1), glyphosate-isopropylammonium (N.6.2), glycosate-potassium ( N.6.3), glyphosate-trimesium (sulfosate), (N.6.4); - N.7 glutamine synthase inhibitors: bilanophos (bialaphos), (N.7.1), bilanaphos-sodium (N.7.2), glufosinate (N. .7.3), glufosinate-P (N.7.4), glufosinate-ammonium (N.7.5);- N.8 DHP synthase inhibitors: asulam (N.8.1);- N.9 Mitosis inhibitors: benfluralin (N. 9.1), butralin (N.9.2), dinitramine (N.9.3), ethalfluralin (N.9.4), fluchloralin (N.9.5), oryzalin (N.9.6), pendimethalin (N.9.7), prodiamine (N.9.8 ), trifluralin (No.9.9); amiprophos (N.9.10), amiprophos-methyl (N.9.11), butamiphos (N.9.12); chlorthal (No.9.13), chlorthal-dimethyl (No.9.14), dithiopyr (No.9.15), thiazopyr (No.9.16), propizamide (No.9.17), tebutame (No.9.18); carbetamide (N.9.19), chlorpropan (N.9.20), flamprop (N.9.21), flamprop-isopropyl (N.9.22), flamprop-methyl (N.9.23), flamprop-M-isopropyl (N.9.24), flurprop-M-methyl (N.9.25), propham (N.9.26);- N.10 VLCFA inhibitors: acetochlor (N.10.1), alachlor (N.10.2), butachlor (N.10.3), dimethachlor (N. 10.4), dimethenamid (N.10.5), dimethenamid-P (N.10.6), metazachlor (N.10.7), metolachlor (N.10.8), metolachlor-S (N.10.9), petoxamide (N.10.10), pretilachlor (No.10.11), propachlor (No.10.12), propisochlor (No.10.13), tenylchlor (No.10.14), flufenacet (No.10.15), mefenacet (No.10.16), difenamid (No.10.17), naproanilide (No.10.18), napropamide (No.10.19), napropamide-M (No.10.20), fentrazamide (No.10.21), anilaphos (No.10.22), cafenstrole (No.10.23), phenoxasulfone (No.10.24), ipfencarbazone (No.10.25), piperophos (No.10.26), pyroxazufon (No.10.27), isoxazoline compounds of the formulas II.1, II.2, II.3, II.4, II.5, II.6, II .7, II.8 and II.9
N.11 Cellulose biosynthesis inhibitors: chlorthiamide (N.11.1), dichlobenil (N.11.2), flupoxam (N.11.3), indaziflam (N.11.4), isoxaben (N.11.5), triaziflam (N.11.6) , 1-cyclohexyl-5-pentafluorophenylaxy-14-[1, 2, 4,6]tiatriazin-3-ylamine ((N.11.7), CAS 175899-01-1);- N.12 Uncoupler herbicides: dinoseb (N.12.1), dinoterb (N.12.2), DNOC (N.12.3), and their salts; - N.13 Auxinic herbicides: 2, 4-D (N.13.1), and its ester salts, claciphos (N.13.2), 2, 4-DB (N.13.3), and its salts and esters, aminocyclopyrachlor (N. .13.4), and its salts and esters, aminopyralide (N.13.5), and its salts, such as aminopyralide-dimethylammonium (N.13.6), aminopyralide-tris(2-hydroxypropyl)ammonium (N.13.7), and its esters , benazolin (No.13.8), benazolin-ethyl (No.13.9), chloramben (No.13.10), and its salts and esters, clmeprop (No.13.11), clopyralide (No.13.12), and its salts and esters, dicamba (N.13.13), and its salts and esters, dichlorprop (N.13.14), and its salts and esters, dichlorprop-P (N.13.15), and its salts and esters, fluroxypyr (N.13.16), fluroxypyr- butomethyl (N.13.17), fluroxypimeptyl (N.13.18), halauxifen (N.13.), and their salts and esters (CAS 943832-60-8); MCPA (N.13.), and its salts and esters, MCPA-thioethyl (N.13.19), MCPB (N.13.20), and its salts and esters, mecoprop (N.13.21), and its salts and esters, mecoprop -P (No.13.22), and its salts and esters, picloram (No.13.23), and its salts and esters, quinclorac (No.13.24), quinmerac (No.13.25), TBA (2, 3, 6), (No.13.26), and its salts and esters, triclopyr (No.13.27), and its salts and esters, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-meth-oxyphenyl) -5-fluoropyridine-2-carboxylic acid (N.13.28), benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate ((N) .13.29), CAS 1390661-72-9); - N.14 Auxin transport inhibitors: diflufenzopyr (N.14.1), diflufenzopyr-sodium (N.14.2), naptalam (N.14.3), and naptalam-sodium (N.14.3) N.14.4);- N.15 Other herbicides: bromobutide (N.15.1), chlorflurenol (N.15.2), chlorflurenol-methyl (N.15.3), cinmethylin (N.15.4), cumiluron (N.15.5), cyclopyrimorate ((N.15.6), CAS 499223-49-3), and its salts and esters, dalapon (N.15.7), dazomet (N.15.8), difenzoquat (N.15.9), dif enzoquat-methylsulfate (No.15.10), dimethipin (No.15.11), DSMA (No.15.12), dimron (No.15.13), endothal (No.15.14), and its salts, etobenzanid (No.15.15), flurenol (No. N.15.16), flurenol-butyl (N.15.17), flurprimidol (N.15.18), fosamine (N.15.19), fosamine-ammonium (N.15.20), indanophan (N.15.21), maleic hydrazide (N.15.22 ), mefluidide (No.15.23), metam (No.15.24), methiozoline ((No.15.25), CAS 403640-27-7), methyl azide (No.15.26), methyl bromide (No.15.27), methyl dimron (N.15.28), methyl iodide (N.15.29), MSMA (N.15.30), oleic acid (N.15.31), oxaziclomephone (N.15.32), pelargonic acid (N.15.33), pyributicarb (N.15.33), N.15.34), quinocamine (N.15.35), tridiphan (N.15.36);O) Insecticides of classes O.1 to O.29-O.1 Acetylcholine esterase (AChE) inhibitors: aldicarb(O.1.1), alanicarb (O.1.2), bendiocarb (O.1.3), benfuracarb (O.1.4), butocarboxim (O.1.5), butoxycarboxim (O.1.6), carbaryl (O.1.7), carbofuran (O.1.8), carbosulfan (O.1.9), etiofencarb (O.1.10), fenobucarb (O.1.11), formetanate (O.1.12), furathiocarb (O.1.13), isocarbate (O.1.14), methiocarb (O.1.15), methomyl (O.1.16), metolcarb (O.1.17), oxamyl (O.1.18), pyrimicarb (O.1.19), propoxur (O.1.20), thiodicarb (O.1.21), thiophanox (O.1.22), trimetacarb (O.1.23), XMC (O.1.24), xylylcarb (O.1.25), and triazamate (O.1.26); acephate (O.1.27), azamethiphos (O.1.28), azinphos-ethyl (O.1.29), azinphosmethyl (O.1.30), cadusaphos (O.1.31), chlorideoxiphos (O.1.32), chlorfenvinphos (O.1.33) , chlormiphos (O.1.34), chlorpyrifos (O.1.35), chlorpyrifos-methyl (O.1.36), coumaphos (O.1.37), cyanophos (O.1.38), demeton-S-methyl (O.1.39), diazinon (O.1.40), dichlorvos/DDVP (O.1.41), dicrotophos (O.1.42), dimethoate (O.1.43), dimethylvinifos (O.1.44), disulfoton (O.1.45), EPN (O.1.46), ethion (O.1.47), ethoprophos (O.1.48), famfur (O.1.49), phenamiphos (O.1.50), fenitrothion (O.1.51), fenthion (O.1.52), phosthiazate (O.1.53), heptenophos (O.1.54), imiciaphos (O.1.55), isofenphos (O.1.56), isopropyl O-(methoxyaminothio-phosphoryl), salicylate (O.1.57), isoxathion (O.1.58), malathion (O.1.59), metarbam (O.1.60), methamidophos (O.1.61), metidation (O.1.62), mevinphos (O.1.63), monocrotophos (O.1.64), naled (O.1.65), ometatoate (O.1.66), oxidemeton -methyl (O.1.67), parathion (O.1.68), parathion-methyl (O.1.69), phentoate (O.1.70), phorate (O.1.71), phosalone (O.1.72) , phosmet (O.1.73), phosphamidon (O.1.74), phoxim (O.1.75), pyrimiphos-methyl (O.1.76), profenophos (O.1.77), propetamphos (O.1.78), prothiophos (O.1.79) ), pyraclophos (O.1.80), pyridaphenthione (O.1.81), quinalphos (O.1.82), sulpotep (O.1.83), tebupirimphos (O.1.84), temephos (O.1.85), terbufos (O.1.86) , tetrachlorvinphos (O.1.87), thiometone (O.1.88), triazophos (O.1.89), trichlorfon (O.1.90), vamidothion (O.1.91);- O.2 GABA:endosulfan dependent chlorine channel antagonists (O.2.1), chlordane (O.2.2); ethiprole (O.2.3), fipronil (O.2.4), flufiprole (O.2.5), pyrafluprole (O.2.6), pyriprole (O.2.7);- O.3 Sodium channel modulators: acrinathrin (O.3.1 ), allethrin (O.3.2), d-cis-trans allethrin (O.3.3), d-trans allethrin (O.3.4), bifenthrin (O.3.5), bioallethrin (O.3.6), bioallethrin S-cyclopentenil ( O.3.7), bioresmethrin (O.3.8), cycloprothrin (O.3.9), cyfluthrin (O.3.10), beta-cyfluthrin (O.3.11), cyhalothrin (O.3.12), lambda-cyhalothrin (O.3.13) , gamma-cyhalothrin (O.3.14), cypermethrin (O.3.15), alpha-cypermethrin (O.3.16), beta-cypermethrin (O.3.17), teta-cypermethrin (O.3.18), zeta-cypermethrin (O. 3.19), cyphenothrin (O.3.20), deltamethrin (O.3.21), empentrin (O.3.22), esfenvalerate (O.3.23), ethofenprox (O.3.24), fenpropathrin (O.3.25), fenvalerate (O.3.26 ), flucitrinate (O.3.27), flumethrin (O.3.28), tau-fluvalinate (O.3.29), halfenprox (O.3.30), heptafluthrin (O.3.31), imiprothrin (O.3.32), meperfluthrin (O. 3.33), methofluthrin (O.3.34), momfluorothrin (O.3.35), permethrin (O.3.36), phen othrin (O.3.37), praletrine (O.3.38), proflutrin (O.3.39), pyrethrin (pyrethrum), (O.3.40), resmethrin (O.3.41), silafluofen (O.3.42), tefluthrin (O.3.40) 3.43), tetramethylfutrin (O.3.44), tetramethrin (O.3.45), tralomethrin (O.3.46), and transfluthrin (O.3.47); DDT (O.3.48), methoxychlor (O.3.49);- O.4 Nicotinic acetylcholine receptor (nAChR) agonists: acetamiprid (O.4.1), clothianidin (O.4.2), cycloxaprid (O.4.3), dinotefuran (O.4.4), imidacloprid (O.4.5), nitenpyram (O.4.6), thiacloprid (O.4.7), thiamethoxam (O.4.8); (2E)-1-[(6-chloropyridin-3-yl), methyl]-N-nitro-2-pentylidene hydrazinecarboximidamide (O.4.9); 1-[(6-chloropyridin-3-yl), methyl]-7-methyl-8-nitro-5-propoxy-1, 2, 3, 5, 6, 7-hexahydroimidazo[1,2-a]pyridine ( O.4.10); nicotine (O.4.11);- O.5 Allosteric receptor activators by nicotinic acetylcholine: spinosad (O.5.1), spinetoram (O.5.2);- O.6 Chloride channel activators: abamectin (O.6.1), benzoate of emamectin (O.6.2), ivermectin (O.6.3), lepimectin (O.6.4), milbemectin (O.6.5);- O.7 Juvenile hormone mimics: hydroprene (O.7.1), quinoprene (O.7.2) ), methoprene (O.7.3); fenoxycarb (O.7.4), pyriproxyfen (O.7.5);- O.8 Non-specific miscellaneous inhibitors (multi-site): methyl bromide (O.8.1), and other alkyl halides; chloropicrin (O.8.2), sulfuryl fluoride (O.8.3), borax (O.8.4), tartar emetic (O.8.5);- O.9 Homopteran selective feed blockers: pymetrozine (O.9.1), flonicamid ( O.9.2);- O.10 Mites growth inhibitors: clofentezine (O.10.1), hexythiazox (O.10.2), diflovidazin (O.10.3); etoxazol (O.10.4);- O.11 Microbial disruptors of insect midgut membranes: proteins from Bt cultures: Cri1Ab, Cri1Ac, Cri1Fa, Cri2Ab, mCry3A, Cry3Ab, Cry3Bb Cry34/35Ab1;- O.12 ATP inhibitors mitochondrial synthase: diafenthiuron(O.12.1); azocyclotin (O.12.2), cyhexatin (O.12.3), fenbutatin oxide (O.12.4), propargite (O.12.5), tetradifon (O.12.6);- O.13 Decouplers of oxidative phosphorylation by means of gradient disruption of protons: chlorfenapyr (O.13.1), DNOC (O.13.2), sulfluramid (O.13.3);- O.14 nicotinic acetylcholine receptor channel blockers (nAChR):bensultap (O.14.1), cartap hydrochloride ( O.14.2), thiocyclam (O.14.3), thiosulap sodium (O.14.4);- O.15 Inhibitors of type 0 chitin biosynthesis: bistrifluron (O.15.1), chlorfluazuron (O.15.2), diflubenzuron (O. 15.3), flucycloxuron (O.15.4), flufenoxuron (O.15.5), hexaflumuron (O.15.6), lufenuron (O.15.7), novaluron (O.15.8), noviflumuron (O.15.9), teflubenzuron (O.15.10) ), triflumuron (O.15.11); - O.16 Inhibitors of chitin biosynthesis type 1: buprofezine (O.16.1); - O.17 Moult disruptors: cyromazine (O.17.1); - O.18 Receptor agonists of ecdysone: methoxifenozide (O.18.1), tebufenozide (O.18.2), halofenozide (O.18.3), fufenozide (O.18.4), cro mafenozide (O.18.5); - O.19 Octopamine receptor agonists: amitraz (O.19.1); - O.20 Inhibitors of the electron transport of the mitochondrial III complex: hydramethylnon (O.20.1), acequinocil (O.20.2) , fluacripyrim (O.20.3);- O.21 Inhibitors of electron transport of mitochondrial complex I: fenazaquin (O.21.1), fenpyroximate (O.21.2), pyrimidifen (O.21.3), pyridaben (O.21.4), tebufenpyrad (O.21.5), tolfenpyrad (O.21.6); rotenone (O.21.7);- O.22 Voltage-dependent sodium channel blockers: indoxacarb (O.22.1), metaflumizone (O.22.2), 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl) ), phenyl]ethylidene]-N-[4-(difluoromethoxy), phenyl]-hydrazinecarboxamide (O.22.3), N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4- [methyl(methylsulfonyl), amino]phenyl]methylene]hydrazinecarboxamide (O.22.4);- O.23 Acetyl-CoA carboxylase inhibitors: spirodiclofen (O.23.1), spiromesifen (O.23.2), spirotetramat (O.23.3.3) );- O.24 Inhibitors of electron transport of the mitochondrial complex IV: aluminum phosphide (O.24.1), calcium phosphide (O.24.2), phosphine (O.24.3), zinc phosphide (O.24.4), cyanide (O.24.5); - O.25 Inhibitors of electron transport of mitochondrial complex II: cyenopyrafen (O.25.1), ciflumetofen (O.25.2); - O.26 Rianodine receptor modulators: flubendiamide (O.26.1), chlorantraniliprole (O.26.2), cyantraniliprole (O.26.3), cyclaniliprol (O.26.4), tetraniliprol (O.26.5); (R)-3-chloro-N1-{2-methyl-4-[1, 2, 2, 2-tetrafluoro-1-(trifluoromethyl), ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl) phthalamide (O.26.6), (S)-3-chloro-N1-{2-methyl-4-[1, 2, 2, 2-tetrafluoro-1-(trifluoromethyl), ethyl]phenyl}-N2-(1 -methyl-2-methylsulfonylethyl), phthalamide (O.26.7), methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole -5-yl]carbonyl}amino), benzoyl]-1,2-dimethyl-hydrazinecarboxylate (0.26.8); N-[4, 6-dichloro-2-[(diethyl-lambda-4-sulfanylidene), carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide (O.26.9); N-[4-Chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazol-3- carboxamide (O.26.10); N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl) pyrazole-3-carboxamide (O.26.11); N-[4, 6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazol- 3-carboxamide (O.26.12); N-[4, 6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)-carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide (O.26.13); N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methyl-phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)- 1H-pyrazole-5-carboxamide (O.26.14); 3-chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazol-5 -carboxamide (O.26.15); 3-bromo-N-[2,4-dichloro-6-(methylcarbamoyl), phenyl]-1-(3,5-dichloro-2-pyridyl)-1H-pyrazole-5-carboxamide (O.26.16); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methyl-phenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H- pyrazole-5-carboxamide (O.26.17); cihalodiamide (O.26.18);- O.27 Active insecticidal compounds of uncertain or unknown mode of action: afidopiren (O.27.1), afoxolaner (O.27.2), azadiractin (O.27.3), amidoflumet (O.27.4), benzoximate (O.27.5), biphenazate (O.27.6), broflanilide (O.27.7), bromopropylate (O.27.8), quinomethionate (O.27.9), cryolite (O.27.10), dichloromezothiaz (O.27.11), dicofol (O.27.12), flufenerin (O.27.13), flomethoquin (O.27.14), fluensulfone (O.27.15), fluhexafon (O.27.16), fluopiram (O.27.17), flupyradifurone (O.27.18), fluralaner ( O.27.19), methoxadiazone (O.27.20), piperonyl butoxide (O.27.21), piflubumide (O.27.22), pyridalyl (O.27.23), pyrifluquinazon (O.27.24), sulfoxaflor (O.27.25), thioxazafen (O.27.26), triflumezopyrim (O 27, 27), 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11 -en-10-one (O.27.28), 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en -2-one (0.27.28), 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl), sulfinyl]; enyl]-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (O.27.29), (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl ]-2-pyridylidene]-2,2,2-trifluoro-acetamide (O.27.31); (E/Z)-N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide (0.27.32); (E/Z)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide (O.27.33); (E/ Z)-N-[1-[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide (O.27.34); (E/ Z)-N-[1-[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide (O.27.35); (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide (O.27.36); (E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoroacetamide(O.27.37); (E/Z)-N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoroacetamide (O.27.38); (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro-propanamide (O.27.39); N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-thioacetamide (O.27.40); N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-N-isopropyl-acetamidine (O.27.41); fluazaindolizine (O.27.42); 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (O.27.43); fluxamethamide (O.27.44); 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole (O.27.45); 3-(benzoylmethylamino)-N-[2-bromo-4-[1, 2, 2, 3, 3, 3-hexafluoro-1-(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro- benzamide (0.27.46); 3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1, 2, 2, 2-tetrafluoro-1-(trifluoromethyl), ethyl]-6-(trifluoromethyl), phenyl]-benzamide ( O.27.47); N-[3-[[[2-iodo-4-[1, 2, 2, 2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl -benzamide (0.27.48); N-[3-[[[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]- 4-fluoro-N-methyl-benzamide (O.27.49); 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1, 2, 2, 2-tetrafluoro-1-(trifluoromethyl)]ethyl]-6-(trifluoromethyl)phenyl]amino ]carbonyl]phenyl]-N-methyl-benzamide (O.27.50); 3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1, 2, 2, 2-tetrafluoro-1-(trifluoromethyl)]ethyl]-6(trifluoromethyl)phenyl]amino] carbonyl]phenyl]-N-methyl-benzamide (0.27.51); 2-chloro-N-[3-[[[2-iodo-4-[1, 2, 2, 2-tetra-fluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl] phenyl]-3-pyridinecarboxamide (0.27.52); 4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1, 2, 2, 3, 3, 3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl ]-2-methyl-benzamide (0.27.53); 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1, 2, 2, 3, 3, 3-hexafluoro-1-( trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide (0.27.54); N-[5-[[2-chloro-6-cyano-4-[1, 2, 2, 3, 3, 3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl] - 4-cyano-2-methyl-benzamide (0.27.55); N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4 -cyano-2-methyl-benzamide (O.27.56); N-[5-[[2-bromo-6-chloro-4-[1, 2, 2, 3, 3, 3-hexafluoro-1-(trifluoromethyl), propyl]phenyl]carbamoyl]-2-cyano-phenyl ]-4-cyano-2-methyl-benzamide (0.27.57); 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1, 2, 2, 3, 3, 3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl ]-2-methyl-benzamide (0.27.58); 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1, 2, 2, 2-tetrafluoro-1-(trifluoromethyl),ethyl]phenyl]carbamoyl]phenyl]-2 -methyl-benzamide (0.27.59); N-[5-[[2-bromo-6-chloro-4-[1, 2, 2, 2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano -2-methyl-benzamide (0.27.60); 2-(1,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; 2-[6-[2-(5-fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine (O.27.61); 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine (O.27.62); N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide (O.27.67); N-ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide (O.27.68); N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propanamide (O.27.69); N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propanamide (O.27.70); N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-methyl-3-methylthio-propanamide (O.27.71); N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3-methylthio-propanamide (0.27.72); 1-[(6-chloro-3-pyridinyl), methyl]-1, 2, 3, 5, 6, 7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2- a]pyridine (O.27.73); 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1, 2, 3, 5, 6, 7-hexahydroimidazo[1,2-a]pyridin-5-ol(O 27.74); 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (0.27.75); 1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (O.27.76); N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole-4-carboxamide (0.27.77); 1-[1-(1-cyanocyclopropyl)-ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (O.27.78); N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (O.27.79); 1-(1,2-dimethyl-propyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (0.27.80); 1-[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide(O.27.81); N-methyl-1-(2-fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (O.27.82); 1-(4,4-difluorocycle) -N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (O.27.83); 1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4- yl-pyrazole-4-carboxamide (O.27.84), N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide (O.27.85); N-cyclopropyl-2-(3 -pyridinyl)-2H-indazole-4-carboxamide (O.27.86); N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide (O.27.87); 2-(3-pyridinyl) )-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide(O.27.88); 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H- indazol-5-carboxamide (O.27.89); methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate (O.27.90); N-[(2,2-difluorocyclopropyl) )methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide (0.27.91); N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide (O.27.92); 2-(3-pyridinyl)-N-(2-pyrimidinylmethyl)-2H-indazol-5-carboxamide (O.27.93); N-[(5-methyl-2-pyrazinyl), methyl] -2-(3-pi ridinyl)-2H-indazole-5-carboxamide (0.27.94), N-[3-chloro-1-(3-pyridyl), pyrazol-4-yl]-N-ethyl-3-(3,3,3,3 - trifluoropropylsulfanyl)propanamide (O.27.95); N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfinyl)propanamide (O.27.96); N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide(O.27.97); N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methyllsulfinyl]-N-ethyl-propanamide (O.27.98); sarolaner (O.27.99), lotilaner (O.27.100).
[0213] The active substances referred to as component 2, their preparation and their activity, for example against harmful fungi, are known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by the IUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48 (6), 587-94, 1968; EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; NOS 3, 296, 272; NOS 3, 325, 503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO 02/22583; WO02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO 03/16286; WO03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO04/83193; WO 05/120234; WO 05/123689; WO 05/ 123690; WO 05/63721; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 10/139271, WO 11/ 028657, WO 12/168188, WO 07/006670, WO 11/77514; WO 13/047749, WO 10/069882, WO 13/047441, WO 03/16303, WO 09/90181, WO 13/007767, WO 13/ 010862, WO 13 /127704, WO 13/024009, WO 13/24010 WO 13/047441 WO 13/162072, WO 13/092224, WO 11/135833, CN 1907024 CN 1456054 CN 103387541 CN 1309897 WO 12/84812 CN 1907024 WO 09094442 WO 14/ 60177 WO 13/116251, WO 08/013622, WO 15/65922 WO 94/01546, EP 2865265 WO 07/129454, WO 12/165511, WO 11/081174, WO 13/47441).
[0214] The present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1), and at least one other active substance useful for the protection of plants, for example, selected from from groups A) to O) (component 2), in particular another fungicide, for example one or more fungicide from groups A) to K) as described above, and if desired, a suitable solvent or solid carrier. These mixtures are of particular interest, since many of them at the same application rate are more efficient against harmful fungi. Furthermore, combating harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to K) as described above is more efficient than combating fungi with individual compounds I or individual fungicides from groups A) to K).
[0215] By applying compounds I together with at least one active substance from groups A) to O) a synergistic effect can be obtained, that is, more than the simple addition of the individual effects (synergistic mixtures) is obtained.
[0216] This can be achieved by applying compounds I and at least one other active substance simultaneously, either together (eg as a tank mix), or separately, or in succession, where the time interval between individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the other active substance(s). The order of application is not essential to the work of the present invention.
[0217] When applying compound I and a pesticide II sequentially, the time between the two applications can vary, for example, between 2 hours and 7 days. A wider range is also possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, and even more preferred of 2 hours to 1 day.
[0218] In binary mixtures and compositions according to the invention, the weight ratio of component 1), and component 2), generally depends on the properties of the active components used, usually in the range of 1 : 10,000 to 10,000 : 1 , is often in the range of 1 : 100 to 100 : 1, regularly in the range of 1 : 50 to 50 : 1, preferably in the range of 1 : 20 to 20 : 1, more preferably in the range of 1 : 10 to 10 : 1, even more preferably in the range from 1 : 4 to 4 : 1 and in particular in the range from 1 : 2 to 2 : 1.
[0219] According to other embodiments of binary mixtures and compositions, the weight ratio of component 1) and component 2) is usually in the range of 1000 : 1 to 1 : 1, often in the range of 100 : 1 to 1 : 1, regularly in the range of 50 : 1 to 1 : 1, preferably in the range of 20 : 1 to 1 : 1, more preferably in the range of 10 : 1 to 1 : 1, even more preferably in the range of 4 : 1 to 1 : 1 and, in particular, in the range of 2 : 1 to 1 : 1.
[0220] According to other embodiments of binary mixtures and compositions, the weight ratio of component 1) and component 2) is normally in the range of 1 : 1 to 1 : 1000, often in the range of 1 : 1 to 1 : 100, regularly in the range of 1 : 1 to 1 : 50, preferably in the range of 1 : 1 to 1 : 20, more preferably in the range of 1 : 1 to 1 : 10, even more preferably in the range of 1 : 1 to 1 : 4 and, in particular, in the range from 1 : 1 to 1 : 2.
[0221] In ternary mixtures, that is, the compositions according to the invention comprising component 1) and component 2) and a compound III (component 3), the weight ratio of component 1) and component 2) depend of the properties of the active substances used, it is generally in the range of 1 : 100 to 100 : 1, regularly in the range of 1 : 50 to 50 : 1, preferably in the range of 1 : 20 to 20 : 1, more preferably in the range of 1 : 10 to 10 : 1 and in particular in the range of 1 : 4 to 4 : 1, and the weight ratio of component 1) and component 3) is generally in the range of 1 : 100 to 100 : 1, regularly in the range of 1 : 50 to 50 : 1, preferably in the range of 1 : 20 to 20 : 1, more preferably in the range of 1 : 10 to 10 : 1 and in particular in the range of 1 : 4 to 4 : 1.
[0222] Any other active components are, if desired, added in a ratio of 20 : 1 to 1 : 20 to component 1).
[0223] These ratios are also suitable for the inventive mixtures applied for seed treatment.
[0224] Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at the Qo site of group A) more preferably selected from compounds (A.1.1), (A .1.4), (A.1.8), (A.1.9), (A.1.10), (A.1.12), (A.1.13), (A.1.14), (A.1.17), (A.1.21 ), (A.1.24), (A.1.25), (A.1.26), (A.1.27), (A.1.30), (A.1.31), (A.1.32), (A.1.34), and (A.1.35); particularly selected from (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1.14), (A.1.17), (A.1.24 ), (A.1.25), (A.1.26), (A.1.27), (A.1.30), (A.1.31), (A.1.32), (A.1.34), and (A.1.35) .
[0225] Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at the Qi site in group A), more preferably selected from the compounds (A.2.1), ( A.2.3), and (A.2.4); particularly selected from (A.2.3) and (A.2.4).
[0226] Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex II in group A), more preferably selected from compounds (A.3.2), (A.3.3 ), (A.3.4), (A.3.7), (A.3.9), (A.3.11), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.18), (A.3.19), (A.3.20), (A.3.21), (A.3.22), (A.3.23), (A.3.24), (A.3.25), (A 3.27), (A.3.28), (A.3.29), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36 ), (A.3.37), (A.3.38), and (A.3.39); particularly selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.12), (A.3.15), (A.3.17), (A.3.19), (A.3.22), (A.3.23), (A.3.24), (A. 3.25), (A.3.27), (A.3.29), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36 ), (A.3.37), (A.3.38), and (A.3.39).
[0227] Preference is also given to mixtures comprising as component 2) at least one active substance selected from other respiration inhibitors in group A), more preferably selected from compounds (A.4.5) and (A.4.11) ; in particular (A.4.11).
[0228] Preference is also given to mixtures comprising as component 2) at least one active substance selected from C14 demethylase inhibitors in group B), more preferably selected from compounds (B.1.4), (B.1.5) ), (B.1.8), (B.1.10), (B.1.11), (B.1.12), (B.1.13), (B.1.17), (B.1.18), (B.1.21), (B.1.22), (B.1.23), (B.1.25), (B.1.26), (B.1.29), (B.1.34), (B.1.37), (B.1.38), (B. .1.43), and (B.1.46); particularly selected from (B.1.5), (B.1.8), (B.1.10), (B.1.17), (B.1.22), (B.1.23), (B.1.25), (B.1.33 ), (B.1.34), (B.1.37), (B.1.38), (B.1.43) and (B.1.46).
[0229] Preference is also given to mixtures comprising as component 2) at least one active substance selected from the inhibitors of Delta14-reductase in group B), more preferably selected from the compounds (B.2.4), (B. 2.5), (B.2.6) and (B.2.8); in particular (B.2.4).
[0230] Preference is also given to mixtures comprising as component 2) at least one active substance selected from phenylamides and acyl amino acid fungicides in group C), more preferably selected from compounds (C.1.1), ( C.1.2), (C.1.4), and (C.1.5); particularly selected from (C.1.1), and (C.1.4).
[0231] Preference is also given to mixtures comprising as component 2) at least one active substance selected from other inhibitors of nucleic acid synthesis in the C group), more preferably selected from compounds (C.2.6), ( C.2.7), and (C.2.8).
[0232] Preference is also given to mixtures comprising as component 2) at least one active substance selected from group D), more preferably selected from compounds (D.1.1), (D.1.2), (D. 1.5), (D.2.4) and (D.2.6); particularly selected from (D.1.2), (D.1.5) and (D.2.6).
[0233] Preference is also given to mixtures comprising as component 2) at least one active substance selected from group E), more preferably selected from compounds (E.1.1), (E.1.3), (E. 2.2) and (E.2.3); in particular (E.1.3).
[0234] Preference is also given to mixtures comprising as component 2) at least one active substance selected from the F group), more preferably selected from the compounds (F.1.2), (F.1.4) and (F. 1.5).
[0235] Preference is also given to mixtures comprising as component 2) at least one active substance selected from the G group), more preferably selected from the compounds (G.3.1), (G.3.3), (G. 3.6), (G.5.1), (G.5.2), (G.5.3), (G.5.4), (G.5.5), (G.5.6), (G.5.7), (G.5.8) , (G.5.9), (G.5.10) and (G.5.11); particularly selected from (G.3.1), (G.5.1), (G.5.2) and (G.5.3).
[0236] Preference is also given to mixtures comprising as component 2) at least one active substance selected from the H group), more preferably selected from the compounds (H.2.2), (H.2.3), (H. 2.5), (H.2.7), (H.2.8), (H.3.2), (H.3.4), (H.3.5), (H.4.9) and (H.4.10); particularly selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9) and (H.4.10).
[0237] Preference is also given to mixtures comprising as component 2) at least one active substance selected from group I), more preferably selected from compounds (I.2.2) and (I.2.5).
[0238] Preference is also given to mixtures comprising as component 2) at least one active substance selected from group J), more preferably selected from compounds (J.1.2), (J.1.5) and (J. 1.8); in particular (J.1.5).
[0239] Preference is also given to mixtures comprising as component 2) at least one active substance selected from the group K), more preferably selected from the compounds (K.1.41), (K.1.42), (K. 1.44), (K.1.45), (K.1.47) and (K.1.49); particularly selected from (K.1.41), (K.1.44), (K.1.45), (K.1.47) and (K.1.49).
[0240] Accordingly, the present invention further relates to mixtures comprising a compound of the formula I (component 1) and a pesticide II (component 2), wherein the pesticide II is selected from the column "Co. 2” from lines B-1 through B-727 of Table B.
[0241] Another embodiment refers to the mixtures B-1 to B-727 listed in Table B in which a line in Table B corresponds in each case to a fungicidal mixture comprising as active components one of the individual compounds of formula I present in this descriptive report, that is, composed of IAA-1 to IAA-503, IBA-1 to IBA-503, ICA-1 to ICA-503, IDA-1 to IDA-503, IEA-1 to IEA-503 , IFA-1 to IFA-503, IGA-1 to IGA-503, IHA-1 to IHA-503, IIA-1 to IIA-503 and IJA-1 to IJA-503 as defined in tables 1 to 11 (component 1 in the column “Co.1”), and the respective pesticide II from groups A) to O) (component 2), indicated in the line in question.
[0242] Another embodiment refers to the mixtures B-1 to B-727 listed in Table B in which a line in Table B corresponds in each case to a fungicidal mixture that comprises as active components one of the compounds Ex-1 to Ex-7 of formula I as defined below in table I (component 1 in column “Co.1”), and the respective pesticide II from groups A) to O) (component 2) indicated in the line in question.
[0243] Preferably, the compositions described in Table B comprise the active components in synergistically effective amounts.TABLE B: MIXTURES COMPRISING AS ACTIVE COMPONENTS, AN INDIVIDUALIZED COMPOUND OF FORMULA I (IN COLUMN CO. 1), AND AS COMPONENT 2) (IN COLUMN CO. 2), A PESTICIDE FROM GROUPS A) FOR THE) [WHICH IS CODED BY EXAMPLE, AS (A.1.1), FOR AZOXISTROBINE AS DEFINED ABOVE].





[0244] Mixtures of active substances can be prepared as compositions that comprise, in addition to the active ingredients, at least one inert ingredient (auxiliary), by usual means, for example, by the means given for the compositions of compounds I. to customary ingredients of such compositions reference is made to the explanations given for compositions containing compounds I.
[0245] The active substance mixtures according to the present invention are suitable as fungicides, as are the compounds of formula I. They are distinguished by an exceptional effectiveness against a wide spectrum of phytopathogenic fungi, especially from the classes of Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn. Oomycetes). Furthermore, it refers to explanations about the fungicidal activity of the compounds and compositions containing compounds I, respectively.I. SYNTHESIS EXAMPLES
[0246] The compounds of formula I can be prepared according to the methods described below.I.1) Preparation of N'-hydroxy-4-[1-(methylamino)ethyl]benzamidine
[0247] To a solution of 4-[1-(methylamino)ethyl]benzonitrile (13 g, 1 eq.) in ethanol (150 mL) was added triethylamine (17.4 g, 2.5 eq.) and hydroxyl amine (9.5 g, 2 eq.). The mixture was refluxed for 3 hours and concentrated under reduced pressure. The crude product (13 g) was used directly without further purification. I.2) Preparation of N-methyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl] phenyl]ethanamine
[0248] A solution of N'-hydroxy-4-[1-(methylamino)ethyl]benzamidine as obtained in step I.1 (35 g, 1.0 eq.) in dichloromethane (400 mL) was treated with trifluoroacetic anhydride (97 g, 3 eq.) at room temperature. The mixture was stirred for 1 hour, before being washed with a saturated aqueous solution of sodium bicarbonate and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product (48 g) was used directly without further purification. I.3) Preparation of N-methyl-N-[1-[4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl]ethyl]acetamide (Ex-16)
[0249] To a solution of N-methyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanamine obtained in step I.2 (8.5 g, 1 eq.) in dichloromethane (100 mL), triethylamine (5.9 g, 2.2 eq.), and acetyl chloride (2.3 g, 1.1 eq.) were added. The mixture was stirred overnight, before being diluted with dichloromethane and washed with 1N aqueous hydrochloric acid. The organic layer was washed successively with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and freed from the solvent under reduced pressure. Flash chromatography on silica gel using cyclohexane - ethyl acetate provided the title product (4.95 g).1H NMR (CDCl3): δ [pm] = 1.5 and 1.65 (d, 3H), 2.15 and 2.25 (s, 3H), 2.7 (s, 3H), 5.25 and 6.15 (q, 1H), 7.45 (m, 2H), 8.13 (m, 2H). I.4) Preparation of N-[[4-[(Z)-N'-hydroxycarbamimidoyl]phenyl]methyl]-N,2-dimethyl-propanamide
[0250] To a solution of N-[(4-cyanophenyl)methyl]-N-methyl-acetamide (8.8 g, 1.0 eq.) in tetrahydrofuran (50 mL) was added hydroxylamine hydrochloride (4 .2 g, 1.5 eq.) and potassium carbonate. (4.5 g, 0.8 eq.) in 20 mL of water. The mixture was stirred overnight at 23°C and the reaction progress was monitored by HPLC. Filtered, washed five times with toluene and concentrated under reduced pressure to give the title compound (10 g), which was used directly without further purification. I.5) Preparation of N,2-dimethyl-N -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (Ex-13)
[0251] A solution of N-[[4-[(Z)-N'-hydroxycarbamimidoyl]phenyl]methyl]-N,2-dimethylpropanamide obtained in step I.4 (10 g, 1.0 eq.) in tetrahydrofuran (100 ml), was treated with trifluoroacetic anhydride (30 g, 3.5 eq.) at room temperature. The mixture was stirred for 2 hours, concentrated under reduced pressure and water was added. The aqueous phase was extracted with ethyl acetate, the combined organic phases were washed with 1N hydrochloric acid and saturated aqueous sodium bicarbonate solution. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate solution to remove trifluoroacetic acid and concentrated under reduced pressure to furnish the title product (3 g). Melting point: 55 °C.6) Preparation of N'-hydroxy-4-[(2-oxopyrrolidin-1-yl)methyl]benzamidine
[0252] To a solution of 4-[(2-oxopyrrolidin-1-yl)methyl]benzonitrile (0.55 g, 1.0 eq.) in ethanol (5 mL) was added hydroxylamine hydrochloride (0.382 g). , 2 eq.) and triethylamine (0.694 g, 2.5 eq.). The mixture was refluxed for 4 hours and concentrated under reduced pressure to obtain the title compound which was used directly without further purification. I.7) Preparation of 1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (Ex-30)
[0253] A solution of N'-hydroxy-4-[(2-oxopyrrolidin-1-yl)methyl]benzamidine obtained in step I.5 (1 g, 1.0 eq.) in dichloromethane (5 mL) was treated with trifluoroacetic anhydride (4.5 g, 5 eq.) at room temperature. The mixture was stirred for 2 hours at 23°C, washed with saturated aqueous sodium bicarbonate solution and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. Flash chromatography on silica gel using cyclohexane - ethyl acetate provided the title product (80 mg). 1H NMR (CDCl3): δ[pm] = 2.1 (m, 2H), 2.45 (m, 2H), 3.3 (m, 3H), 4.5 (s, 2H), 7.4 (m, 2H), 8.13 (m, 2H).
[0254] The compounds Ex-1 to Ex-34 listed in Table I were prepared in an analogous manner. WHERE A IS NOT REPLACED, AND WHERE THE MEANING OF R1,R2, R3 AND R4 ARE AS DEFINED IN EACH LINE, AND WHERE # DENOTES THE CONNECTION POINT OF THE NR1R2 GROUP TO THE CR3R4 PORTION

HPLC: High Performance Liquid Chromatography; KinetexXB C18 1.7 µ HPLC column (50 x 2.1 mm); eluent: acetonitrile/water + 0.1% trifluoroacetic acid (gradient from 5 : 95 to 100 : 0 in 1.5 min at 60 °C, flow gradient from 0.8 to 1.0 mL/min in 1, 5 min). MS: Quadrupole Electron Spray Ionization, 80 V (positive mode). Rt: retention time in minutes.II. BIOLOGICAL EXAMPLES FOR FUNGICIDAL ACTIVITYIII. 4] The fungicidal action of the compounds of formula I was demonstrated by the following experiments:A. Glass House Tests
[0255] The spray solutions were prepared in several steps: The stock solution was prepared: a mixture of acetone and/or dimethylsulfoxide and the wettol wetting agent/emulsifier, which is based on ethoxylated alkylphenols, in a ratio ( volume) of 99 to 1 solvent-emulsifier was added to 25 mg of the compound to give a total of 5 ml. Water was then added to the total volume of 100 ml. This stock solution was diluted with the solvent-emulsifier-water mixture described for the given concentration.11. 1) Curative control of soybean rust on soybeans caused by Phakopsora pachyrhizi
[0256] Potted soybean seedling leaves were inoculated with spores of Phakopsora pachyrhizi. To ensure the success of the artificial inoculation, the plants were transferred to a humid chamber with a relative humidity of about 95% and 20 to 24°C for 24 hours. The next day, the plants were grown for 3 days in a greenhouse chamber at 23 to 27 °C and relative humidity between 60 and 80%. Then, the plants were sprayed to drain with an aqueous suspension, containing the concentration of active ingredient or its mixture as described below. The plants were allowed to air dry. Then, the experimental plants were grown for 14 days in a greenhouse at 23 to 27 °C and relative humidity between 60 and 80%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
[0257] In this test, plants that were treated with 32 ppm of the active compound Ex-1, Ex-4, Ex-5, Ex-6, Ex-7, Ex-8, Ex-9, Ex-10, Ex -11, Ex-12, Ex-13, Ex-14, Ex-15, Ex-16, Ex-18, Ex-19, Ex-21, Ex-22, Ex-23, Ex-28, Ex-30 , Ex-31, Ex-32 and Ex-33 showed a diseased leaf area of at most 5%, while untreated plants had 90% diseased leaf area.11.2) Protective control of soybean rust on soybeans caused by Phakopsora pachyrhizi Potted soybean seedling leaves were sprayed to drain with an aqueous suspension, containing the concentration of active ingredient or its mixture as described below. The plants were allowed to air dry. The experimental plants were grown for 2 days in a greenhouse at 23 to 27 °C and relative humidity between 60 and 80%. The plants were then inoculated with spores of Phakopsora pachyrhizi. To ensure the success of the artificial inoculation, the plants were transferred to a humid chamber with a relative humidity of about 95% and 20 to 24 °C for 24 hours. The experimental plants were grown for fourteen days in a greenhouse between 23 and 27 °C and relative humidity between 60 and 80%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
[0258] In this test, plants that were treated with 32 ppm of the active compound Ex-1, Ex-4, Ex-5, Ex-6, Ex-7, Ex-8, Ex-9, Ex-10, Ex -11, Ex-12, Ex-13, Ex-14, Ex-15, Ex-16, Ex-17, Ex-18, Ex-19, Ex-20, Ex-21, Ex-22, Ex-23 , Ex-28, Ex-29, Ex-30, Ex-31, Ex-32 and Ex-33 showed 0% diseased leaf area, while untreated plants had 90% diseased leaf area.
[0259] In this test, plants that were treated with 16 ppm of the active compound Ex-24, Ex-25, Ex-26 and Ex-27 showed a diseased leaf area of 0%, while untreated plants showed 90% of diseased leaf area. 11.3) Curative control of brown rust in wheat caused by Puccinia recondita
[0260] The first two leaves developed from potted wheat seedlings were dusted with spores of Puccinia recondita. To ensure the success of the artificial inoculation, the plants were transferred to a moist chamber without light and with a relative humidity of 95 to 99% and 20 to 24°C for 24 hours. The next day, the plants were grown for 3 days in a greenhouse chamber at 20 to 24 °C and relative humidity between 65 and 70%. Then, the plants were sprayed to drain with an aqueous suspension, containing the concentration of active ingredient or its mixture as described below. The plants were allowed to air dry. Then, the experimental plants were grown for 8 days in a greenhouse chamber at 20 to 24 °C and relative humidity between 65 and 70%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
[0261] In this test, plants that were treated with 63 ppm of the active compound Ex-1, Ex-4, Ex-5, Ex-7, Ex-8, Ex-9, Ex-10, Ex-11, Ex -12, Ex-13, Ex-14, Ex-15, Ex-16, Ex-18, Ex-19, Ex-21, Ex-23, Ex-31 and Ex-33 showed a maximum diseased leaf area of 2 %, while untreated plants had 90% diseased leaf area.11.4) Preventive control of brown rust in wheat caused by Puccinia recondita
[0262] The first two leaves developed from pot-grown wheat seedlings were sprayed to drain with an aqueous suspension, containing the concentration of active ingredient or its mixture as described below. Seven days later the plants were inoculated with spores of Puccinia recondita. To guarantee the success of the artificial inoculation, the plants were transferred to a humid chamber without light and relative humidity of 95 to 99% and 20 to 24 °C for 24 hours. Then, the experimental plants were grown for 6 days in a greenhouse chamber at 20 to 24 oC and a relative humidity between 65 and 70%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
[0263] In this test, plants that were treated with 63 ppm of the active compound Ex-4, Ex-5, Ex-8, Ex-9, Ex-10, Ex-11, Ex-12, Ex-13 and Ex -14 showed a diseased leaf area of at most 12%, while untreated plants had 90% diseased leaf area.

权利要求:
Claims (13)
[0001]
1. COMPOUNDS OF FORMULA I
[0002]
COMPOUNDS OF FORMULA I according to claim 1, characterized in that R3 is H, and R4 is CF3.
[0003]
3. COMPOUNDS OF FORMULA I, according to any one of claims 1 to 2, characterized in that R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C(=O )-(C1-C6 alkyl), C(=O)-(C1-C6 alkoxy), phenyl-C1-C4 alkyl, heteroaryl-C1-C4 alkyl, phenyl, naphthyl or a saturated, partially unsaturated mono- or bicyclic heterocycle with 3 to 10 members, wherein the ring member atoms of said mono- or bicyclic heterocycle include, in addition to carbon atoms, a further 1, 2, 3 or 4 heteroatoms selected from N, O and S as member atoms of the ring and wherein 1 or 2 of the carbon ring member atoms of the heterocycle may be substituted by 1 or 2 groups independently selected from C(=O) and C(=S); and wherein the heteroaryl group in the heteroaryl-C1-C4 alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include, in addition to carbon atoms, 1, 2, 3 or 4 selected heteroatoms from N, O and S as ring member atoms; and wherein any of the aforementioned aliphatic or cyclic groups are unsubstituted or substituted with 1, 2, 3 or up to the maximum possible number of identical or different R1a groups; as defined in claim 1; and R2 is C(=O)-(C1-C6 alkyl), or C(=O)-(C1-C6 alkoxy).
[0004]
4. COMPOUNDS OF FORMULA I according to any one of claims 1 to 2, characterized in that R1 and R2 independently of one another are hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, C(=O)-(C1-C6 alkyl), C(=O)-(C1-C6 alkoxy), phenyl-C1-C4 alkyl, or phenyl; and wherein any of the cyclic or aliphatic groups are unsubstituted or substituted with 1, 2, 3, 4 or more up to a maximum possible number of identical or different groups of R 1a as defined in claim 1.
[0005]
5. COMPOUNDS OF FORMULA I
[0006]
6. COMPOUNDS OF FORMULA I according to claim 5, characterized in that R1 and R2 together with the nitrogen atom to which they are attached form a 3- to 7-membered saturated or partially unsaturated mono- or bicyclic heterocycle, wherein the heterocycle includes, in addition to a nitrogen atom and one or more carbon atoms, 1, 2 or 3 heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=O), and C(=S); and wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different R1a groups; wherein R1a is halogen, cyano, NO2, OH, SH, NH2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkyl , NHSO2-C1-C4 alkyl, (C=O)-C1-C4 alkyl, C(=O)-C1-C4 alkoxy or C1-C6 haloalkylsulfonyl.
[0007]
7. COMPOUNDS OF FORMULA I according to claim 5, characterized in that R 1 and R 2 together with the nitrogen atom to which they are attached form a 5- to 7-membered saturated or partially unsaturated heterocycle, wherein the heterocycle includes, in addition to a nitrogen atom and one or more carbon atoms, no other heteroatoms or 1 or 2 heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=O), and C(=S); and wherein the heterocycle is unsubstituted or carries 1, 2, 3, 4 or up to the maximum possible number of identical or different R1a groups; wherein R1a is halogen or C1-C6 alkyl.
[0008]
8. COMPOUNDS OF FORMULA I according to claim 5, characterized in that R 1 and R 2 together with the nitrogen atom to which they are attached form a saturated or partially unsaturated 3- to 6-membered heterocycle, in which one or two groups CH2 of the heterocycle can be substituted by one or two groups independently selected from the group of C(=O), and C(=S).
[0009]
9. MIXTURE, characterized in that it comprises at least one compound of formula I, as defined in any one of claims 1 to 5, and at least one other active substance as a pesticide selected from the group consisting of herbicides, phytotoxicity protectants, fungicides , insecticides and plant growth regulators.
[0010]
10. AGROCHEMICAL COMPOSITION, characterized in that it comprises an auxiliary and at least one compound of formula I, or an N-oxide, or an agriculturally acceptable salt thereof, as defined in any one of claims 1 to 5.
[0011]
11. AGROCHEMICAL COMPOSITION, according to claim 10, characterized in that the auxiliary is selected from the group consisting of anionic, cationic and non-ionic surfactants.
[0012]
12. AGROCHEMICAL COMPOSITION according to any one of claims 10 to 11, characterized in that it further comprises seed, in which the amount of the compound of formula I, or an N-oxide, or an agriculturally acceptable salt thereof, is 0. 1 g to 10 kg per 100 kg of seed.
[0013]
13. METHOD FOR COMBATING HARMFUL PHYTOPATHOGENIC FUNDS, characterized in that it comprises treating the plants, soil or seeds to be protected against a fungal attack, with an effective amount of at least one compound of formula I, or an N-oxide, or a an agriculturally acceptable salt thereof as defined in any one of claims 1 to 5.

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同族专利:

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公开号 | 公开日

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EA201891146A1|2018-12-28|

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JP2018537457A|2018-12-20|

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US10674727B2|2020-06-09|

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IL259152D0|2018-07-31|

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MX2018006244A|2018-11-09|

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CN108289449A|2018-07-17|

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CO2018005384A2|2018-05-31|

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AR106763A1|2018-02-14|

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KR20180083419A|2018-07-20|

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US20180368409A1|2018-12-27|

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BR112018008449A2|2018-11-06|

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WO2017085100A1|2017-05-26|

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EP3376868A1|2018-09-26|

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AU2016354902A1|2018-05-10|

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CA3003949A1|2017-05-26|

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CL2018001350A1|2018-06-22|

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ZA201803948B|2019-09-25|

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法律状态:
2019-12-03| B06U| Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette]|

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2021-06-08| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|

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2021-07-06| B16A| Patent or certificate of addition of invention granted|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 16/11/2016, OBSERVADAS AS CONDICOES LEGAIS. |

优先权:

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申请号 | 申请日 | 专利标题

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EP15195439|2015-11-19|

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EP15195439.3|2015-11-19|

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PCT/EP2016/077819|WO2017085100A1|2015-11-19|2016-11-16|Substituted oxadiazoles for combating phytopathogenic fungi|

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